molecules ISSN by MDPI
|
|
- Melvyn McGee
- 5 years ago
- Views:
Transcription
1 Molecules 2000, 5, molecules ISS by MDPI Reactions with Hydrazonoyl Halides. 31. Synthesis of Some ew Pyrrolidino[3,4-c]pyrazolines, Pyrazoles, and Pyrazolo[3,4-d]pyridazines Abdou. Abdelhamid 1 *, Hussien F. Zohdi 2, Mohamed M. M. Sallam 1 and agla A. Ahmed 1 1 Department of hemistry, Faculty of Science, airo University, Giza 12613, Egypt ABDU@main-scc.cairo.eun.eg 2 Department of hemistry, United Arab Emirates University, Al-Ain 17551, UAE * Author to whom correspondence should be addressed. For part 30 see [1]. Received: 29 May 2000; revised form 6 July 2000 / Accepted: 6 July 2000 / Published: 21 July 2000 Abstract: Pyrrolidino[3,4-c]pyrazoline and pyrazole derivatives were synthesized via reactions of a substituted hydrazonoyl bromide with -arylmaleimides and active methylene reagents, respectively. Synthesized pyrazoles were reacted with hydrazine hydrate to give the corresponding pyrazolo[3,4-d]pyridazines. Keywords: hydrazonoyl halides, -arylmaleimides, pyrrolidino[3,4-c]pyrazolines, pyrazoles, pyrazolo[3,4-d]pyridazines. Introduction Hydrazonoyl halides have been widely employed in the synthesis of heterocyclic derivatives [2-5]. In continuation of our interest in the synthesis of heterocyclic systems containing a pyrazole moiety [6-10], we report herein a facile synthesis of pyrrolidino[3,4-c]pyrazoline, pyrazole, and pyrazolo[3,4- d]pyridazine derivatives. Results and Discussion Treatment of the hydrazonoyl bromide 1 [10] with the appropriate -arylmaleimides 2a-c in benzene containing triethylamine afforded pyrrolidino[3,4-d]pyrazolines 3a-c (cf. Scheme 1). The structures of compounds 3a-c were confirmed by their spectroscopic data. For example, the 1 H MR spectrum of 3a
2 Molecules 2000, showed signals at δ = 1.11 (t, 3H, H 3 H 2 ); 2.33 (s, 3H, H 3 ); 2.41 (s, 3H, H 3 ); 4.12 (q, 2H, H 2 H 3 ); 5.20 (d, J=7Hz, 1H, pyrazoline H-4); 5.49 (d, J=7Hz, 1H, pyrazoline H-5) and (m, 13H, ArH). The IR spectra of 3a-c were characterized by two widely separated bands in the region cm -1 assigned the -Ar- grouping [11]. Also, the hydrazonoyl bromide 1 was reacted with each of malononitrile, ethyl cyanoacetate, dibenzoylmethane, benzoylacetonitrile, acetoacetanilide, and ω-benzenesulfonylacetophenone in ethanolic sodium ethoxide to give substituted pyrazoles 4a-g (Scheme 1). Structures 4a-g were confirmed on the basis of spectral data. For example, the IR spectrum of compound 4c revealed bands at 1720, 1685, 1660 cm -1 ( groups) and its 1 H MR spectrum showed signals at δ = 1.23 (t, 3H, H 3 H 2 ); 2.32 (s, 3H, H 3 ); 2.39 (s, 3H, H 3 ); 4.24 (q, 2H, H 2 H 3 ); (m, 18H, ArH). R Ar R Br H R Et 2 l 3 l 1 l 4 R = H 3 H3 3 a, Ar = 6 b, Ar = 4-H 3 6 H 4 c, Ar = 4- H 3 6 H 4 4a, =, = H 2 b, = 2 2, = H 2 c, = 6, = 6 d, =, = 6 e, = 6 H, = H 3 f, = S 2 6, = 6 g, = S 2 6, = R Scheme 1. Pyrazoles 4a,b and 4d-g were converted to the corresponding pyrazolo[3,4-d]pyridazines 6a,b and 6d-g, respectively, on boiling under reflux with hydrazine hydrate in ethanol. The structure of the products could conceivably be formulated as either 5 or 6. Based on analytical analyses and spectral data, structures 5 were ruled out. The formation of the products of type 6 can be explained via elimination of water, to give the hydrazone intermediate 7, which then readily cyclized to product 6 (cf. Scheme 2). Alternatively, the formation of the product can be explained by formation of the hydrazide 8, followed by elimination of water to give pyrazolo[3,4-d]pyridazines 6. All attempts to isolate intermediates 7 and 8 were unsuccessful.
3 Molecules 2000, Et 2 H 3 l H 3 4 H 2 Et 2 H 3 H 2 H H 3 l l H 3 H Et 2 z H 3 H l H 3 l H 3 5 H 3 6 6a, =, = H 2 b, = 2 2, = H 2 d, =, = 6 e, = 6 H, = H 3 f, = 6 S 2, = 6 g, = 6 S 2, = R Scheme 2.
4 Molecules 2000, Experimental General All melting points were determined on an Electrothermal apparatus and are uncorrected. IR spectra were recorded (KBr discs) on a Shimadzu FT-IR 8201 P spectrophotometer. 1 H MR spectra were recorded in Dl 3 on a Varian Gemini 200 MHz spectrometer and chemical shifts are expressed in δ units using TMS as an internal reference. Elemental analyses were carried out at the Microanalytical enter of the University of airo, Giza, Egypt. Hydrazonoyl bromides 1 [10] and -arylmaleimides 2ac [12] were prepared as previously reported. General procedure for the synthesis of 5-aryl-1-(4-chlorophenyl)-3-[3 -ethoxycarbonyl-5 -methyl-1 - (4-tolyl)-4 -pyrazoloyl]pyrrolidino[3,4-c]pyrazoline-4,6-diones (3a-c) A solution of the substituted hydrazonoyl bromide 1 (2.5 g, mmol), the appropriate - arylmaleimides 2a-c (0.005 mol) and triethylamine (0.7 ml, mol) in dry benzene (20 ml) was refluxed for 3 h. The solvent was removed under vacuum and the residue triturated with petroleum ether (b.p. 40/60 o, 10 ml). The resulting solid was collected, washed and crystallized from acetic acid or ethanol to give 3a-c (cf. Table 1). General procedure for the synthesis of 4,5-disubstituted 1-(4-chlorophenyl)- 3-[3 -ethoxy-carbonyl-5 - methyl-1 -(4-tolyl)-4 -pyrazoloyl]pyrazoles (4a-g) The appropriate active methylene compound (malononitrile, ethyl cyanoacetate dibenzoylmethane, benzoylacetonitrile, acetoacetanilide, ω-benzenesulfonylacetophenone, or ketosulfone. (0.005 mol) was added to an ethanolic sodium ethoxide solution [prepared from sodium metal (0.11 g-atom) in absolute ethanol (20 ml)]. After stirring for 10 minutes, the hydrazonoyl bromide 1 (2.5 g, mol) was added and stirring was continued for an additional 30 minutes. The reaction mixture was left overnight at room temperature and the precipitated product was collected by filtration. The solid was washed with water and recrystallized from ethanol to give the corresponding pyrazoles 4a-g, respectively (cf. Table 1). General procedure for the synthesis of 4,5-disubstituted 4-[1-(4-chlorophenyl)-3-pyrazolyl]-2,6- dihydro-3-methyl-2-(4-tolyl)-pyrazolo[3,4-d]pyridazin-7-ones (6a,b,d-g) The appropriate pyrazoles (4a,b and 4d-g) (0.005 mol) in a mixture of ethanol (20 ml) and hydrazine hydrate (0.75 ml, mol) were refluxed for 4h, during which time the pyrazole dissolved and the corresponding pyrazolo[3,4-d]pyridazine precipitated. The latter was collected, washed with water and recrystallized from ethanol or dimethylformamide to give 6a,b,d-g (cf. Table 1).
5 Molecules 2000, Table 1. Analytical data of the newly synthesized compounds. ompd no. 3a 3b 3c olor ellowish green ellowish green ellowish green ield % M.P., o Solvent EtH EtH AcH 4a ellow EtH 4b olorless EtH 4c ellow EtH 4d ellow EtH 4e ellow EtH 4f ellow EtH 4g Brown EtH 6a range EtH 6b ellow EtH 6d olourless EtH 6e olourless EtH 6f ellow EtH 6g ellow EtH Mol.Formula % Analyses, alcd. /Found Mol.Wt. H S 32 H 26 l H 28 l H 28 l H 21 l H 26 l H 29 l H 24 l H 28 l H 29 l 4 5 S H 39 l 6 7 S H 17 l H 22 l H 20 l H 24 l H 25 l 6 3 S H 35 l 8 5 S
6 Molecules 2000, Table 2. IR and 1 H-MR spectroscopic data. omp IR (cm -1 ) no. 3a and ( s) 3b and ( s) 4a 3292,3176 (H 2 ); 2229 (); 737, 1659 ( s). 4b 3272, 3185 (H 2 ), 1730, 1647 ( s). 1 H MR (δ ppm) 1.11 (t, 3H, H 2 H 3 ); 2.33 (s, 3H, H 3 ); 2.41 (s, 3H, H 3 ); 4.12 (q, 2H, H 2 H 3 ); 5.20 (d, 1H, pyrazoline H-4); 5.49 (d, 1H, pyrazoline H-5) and (m, 13H, ArH) (t, 3H, H 2 H 3 ); 2.33 (s, 3H, H 3 ); 2.41 (s, 6H, 2H 3 ); 4.12 (q, 2H, H 2 H 3 ); 5.02 (d, 1H, pyrazoline H-4); 5.49 (d, 1H, pyrazoline H-5) and (m, 12H, ArH). 3c and ( s) 1.11 (t, 3H, H 2 H 3 ); 2.33 (s, 3H, H 3 ); 2.41 (s, 3H, H 3 ); 4.92 (s, 3H, H 3 ); 4.12 (q, 2H, H 2 H 3 ); 5.02 (d, 1H, pyrazoline H-4); 5.49 (d, 1H, pyrazoline H-5) and (m, 12H, ArH) (t, 3H, H 2 H 3 ); 2.40 (s, 3H, H 3 ); 2.43 (s, 3H, H 3 ); 4.01 (q, 2H, H 2 H 3 ); 7.14 (s, br., 2H, H 2 ) and (m, 8H, ArH s) (t, 3H, H 2 H 3 ); 1.10 (t, 3H, H 2 H 3 ); 2.40 (s, 3H, H 3 ); 2.43 (s, 3H, H 3 ); 4.01 (q, 2H, H 2 H 3 ); 4.21 (q, 2H, H 2 H 3 ); 7.14 (s, br., 2H, H 2 ) and (m, 8H, ArH). 4c 1720, 1685, 1660 ('s) 1.23 (t, 3H, H 2 H 3 ); 2.32 (s, 3H, H 3 ); 2.39 (s, 3H, H 3 ); 4d 2236 (); 1724, 1658 ( s). 4e 3240 (H); 1735, 1668 ( s). 4f 4g 1730,1667 ( s); 1314,1140 (S 2 ). 1730, 1667 ( s) and 1314, 1140 (S 2 ). 6a 3340, 3292, 3176 (H 2, H); 2220 (); 1668 () 6b 3244 (H); 1710, 1666 () (q, 2H, H 2 H 3 ); (m, 18H, ArH) (t, 3H, H 2 H 3 ); 2.42 (s, 3H, H 3 ); 2.49 (s, 3H, H 3 ); 4.13 (q, 2H, H 2 H 3 ); and (m, 13H, ArH) (t, 3H, H 2 H 3 ); 2.41 (s, 3H, H 3 ); 2.50 (s, 3H, H 3 ); 2.75 (s, 3H, H 3 ); 4.03 (q, 2H, H 2 H 3 ); (m, 13H, ArH) and (s, br., 1H, H) (t, 3H, H 2 H 3 ); 2.34 (s, 3H, H 3 ); 2.44 (s, 3H, H 3 ); 4.03 (q, 2H, H 2 H 3 ); and (m, 18H, ArH) (t, 3H, H 2 H 3 ); 1.14 (t, 3H, H 2 H 3 ); 2.39 (s, 6H, 2H 3 ); 2.43 (s, 6H, H 3 ); 4.02 (q, 2H, H 2 H 3 ); 4.12 (q, 2H, H 2 H 3 ) and (m, 17H, ArH) (s, 3H, H 3 ); 2.55 (s, 3H, H 3 ); 6.90 (s, 2H, H 2 ); (m, 8H, ArH) and (s, 1H, H) (t, 3H, H 2 H 3 ); 2.39 (s, 3H, H 3 ); 2.67 (s, 3H, H 3 ); 4.12 (q, 2H, H 2 H 3 ); 6.22 (s, 2H, H 2 ) and (m, 8 H, ArH); (s, 1H, H). 6d 3345 (H); 2233 (); 1674 () (s, 3H, H 3 ); 2.67 (s, 3H, H 3 ); (m, 13H, ArH) and (s, 1H, H). 6e 3244 (H); 1666 () 2.39(s, 3H, H 3 ); 2.67(s, 3H, H 3 ); 2.42(s, 3H, H 3 ); (m, 13H, ArH); 10.62(s, 1H, H) and (s, 1H, H) 6f 6g 3222 (H); 1663 (); 1314, 1140 (S 2 ) (H); 1663 (); 1314, 1140 (S 2 ) (s, 3H, H 3 ); 2.44 (s, 3H, H 3 ); (m, 18H, ArH) and (s, 1H, H). Insoluble
7 Molecules 2000, References and otes 1. Abdelhamid, A..; Rateb,.M.; Dawood, K.M. Phosph., Sulfur, Silicon, and Related Elements 2000, in press. 2. Ulrich, H. The hemistry of Imidoyl Halides; Plenum Press: ew ork, 1968: p Huisgen, R.; Garashey, R.; Sauer, J. The hemistry of Alkenes; Patai, S., Ed.; Wiley-Interscience: ew ork,.., 1964; Vol. 1, p Abdelhamid, A.. J. hem. Res (S) 208, (M) Butler, R..; Scott, F.L. hem. Ind. (London) 1970, Hassan,.M.; Abdelhamid, A.. J. hem. Res. 1997, (S) 350, (M) 2254 (1997). 7. Hassan,.M.; Fahmi, A.A.; Abd-El-mageid, F.F.; Abdelhamid, A.. J. hin. hem. Soc. 1996, 43, Abdelhamid, A..; Abd-El-mageid, F.F.; Hassan,.M.; Zohdi, H.F. J. hem. Res (S), 492, (M) Abdelhamid, A..; Attaby, F.A.; Khalifa, F.A.; Ghabrial, S. S. Arch. Pharm. Res. 1992, 15, Abdelhamid, A..; Zohdi, H.F.; Sallam, M.M.M.; Ahmed,.A. Phosph., Sulfur, Silicon, and Related Elements 2000, in press. 11. Abdelhamid, A..; Ghabrial, S.S. Sulfur Letters 1987, 7, Searle,.F.E. U.S. Pat, 2,444,536 (to E.I. Dupont De emours and o. Inc.), 1948; [hem. Abstr. 1949, 42, 7340c]. Sample Availability: Available from MDPI by MDPI (
β-oxo anilides in heterocyclic synthesis: Synthesis of tri- and tetracyclic heteroaromatic containing a bridgehead nitrogen atom
RIGIAL ARTICLE rg. Commun. 2:3 (2009) 66-71 β-xo anilides in heterocyclic synthesis: ynthesis of tri- and tetracyclic heteroaromatic containing a bridgehead nitrogen atom Abdel H. M. Hussein *, Mohamed.
More informationGeneral Papers ARKIVOC 2004 (i) 71-78
General Papers ARKIVC 2004 (i) 71-78 Synthesis of 1,3,5-triazepine-2,4-dione, pyrrolo[3,4-f] [1,3,5]triazepine-2,4-dione, pyridazino[4,5-f][1,3,5]triazepine and 1,3,5,7,9-pentazaheptaline derivatives..
More informationJournal of Asian Scientific Research (2,4- DIOXO-1,4 - DIHYDRO - 2H - QUINAZOLIN YL) - ACETIC ACID HYDRAZIDE: SYNTHESIS AND REACTIONS
Journal of Asian Scientific Research journal homepage: http://aessweb.com/journal-detail.php?id=5003 (2,4- DIX-1,4 - DIYDR - 2 - QUIAZLI - 3 - YL) - ACETIC ACID YDRAZIDE: SYTESIS AD REACTIS Ahmed Mohamed
More informationJournal of Global Pharma Technology
Journal of Global Pharma Technology ISS: 0975-8542 Available nline at www.jgpt.co.in RESEARCH ARTICLE Synthesis, Characterization of Some ew Heterocyclic Derivatives Asstabraq Mohsin Yasir Department of
More informationSupplementary Materials. Table of contents
Supplementary Materials Microwave- Assisted Multicomponent Ecofriendly Synthesis of 3-Bihetaryl-2-oxindole Derivatives Grafted with Phenothiazine Moiety A. S. Al-Bogami 1 and A. S. El-Ahl 1,2 * 1 Chemistry
More informationScheme 1. Received October 18, J. Heterocyclic Chem., 42, 1185 (2005).
Sep-Oct 2005 Studies on Enaminonitriles: a New Synthesis of 1,3-Substituted Pyrazole-4-carbonitrile Said Ahmed Soliman Ghozlan 1, Ismail Abdelshafy Abdelhamid 1, Hatem Moustafa Gaber 2 and Mohamed Hilmy
More informationA SIMPLE AND EFFICIENT ROUTE TO CYCLOALKENE- FUSED 2,3-DIHYDROPHTHALAZINE-1(4H),4-DIONES
A SIMPLE AD EFFICIET RUTE T CYCLALKEE- FUSED 2,3-DIHYDRPHTHALAZIE-1(4H),4-DIES orbert Haider *, Emilia Mavrokordatou and Andreas Steinwender Institute of Pharmaceutical Chemistry, University of Vienna,
More informationIssue in Honor of Prof. C. D. Nenitzescu ARKIVOC 2002 (ii)
Facile bromination of the benzene ring during the cyclisation of the 1H-3-methyl-4-ethoxycarbonyl-5- -arylidenehydrazonopyrazoles to the 3-substituted-aryl-1H-6-methyl-7-ethoxycarbonyl- -pyrazolo[3,2-c]-s-triazoles
More informationSynthesis and Structural Studies of 3-Imino-5-Dimethylamino- 7-Aryl/Alkylimino-1,2,4,6 Thiatriazepines
IJP Vol. 6, o,2, Mar-April 2017 I:2319-6602 M.R Ugale 1 B..Berad 2 1 Department of Applied hemistry, GHRIET, agpur, India. 2 Post Graduate Department of hemistry, RTMU, agpur, India. orresponding Author:
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
More informationmolecules ISSN
Molecules 2006, 11, 43-48 molecules ISS 1420-3049 http://www.mdpi.org Synthesis of Some ew 2-(3-Aryl-1-phenyl-4-pyrazolyl)- benzoxazoles Using Hypervalent Iodine Mediated Oxidative Cyclization of Schiff
More informationSynthesis of Novel Fused Heterocycles Based on Pyrano[2,3-c]pyrazole
Molecules 1998, 3, 71 79 molecules ISS 1420-3049 Synthesis of ovel Fused eterocycles Based on Pyrano[2,3-c]pyrazole M. E. A. Zaki ational Research entre, Dokki, airo, Egypt Tel: 002-02 5838479, Fax: 002-02-3370931
More informationReactions of 2,4-diphenylbutadiene-1,4-sultone with some 1,2- and 1,3-nitrogen binucleophiles
General Papers ARKIVC 206 (iii) 5-22 Reactions of 2,4-diphenylbutadiene-,4-sultone with some,2- and,3-nitrogen binucleophiles Korany A. Ali, a * Anne Jäger, b and Peter Metz b a Applied rganic Chemistry
More informationmolecules ISSN
Molecules 2000, 5, 816-825 molecules ISS 1420-3049 http://www.mdpi.org Synthesis of Sultam Derivatives with Expected Biological Activity. 15 S.H. Doss 1, V.B. Baghos 2, A.. Abdelhamid 2 * and M.M.A. Halim
More informationReactions with the Arylhydrazones of a-cyanoketones: Utility of Arylhydrazonomesoxalonitriles for the Synthesis of Azoles and Azolines
Reactions with the ylhydrazones of a-cyanoketones: Utility of ylhydrazonomesoxalonitriles for the Synthesis of Azoles and Azolines Ebtisam Abdel Aziz Hafez*, Mohamed Ali Elsayed Khalifa, Sayed Kamel Ahmed
More informationSynthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine Hydrate in Aqueous Medium
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Synthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine
More informationSerendipitous synthesis of 1,4-benzothiazin derivatives using 2-[(2-aminophenyl)disulfanyl]aniline
erendipitous synthesis of 1,4-benzothiazin derivatives using 2-[(2-aminophenyl)disulfanyl]aniline Mohammad Reza Islami a *, Fouziyeh Mollazehi a, Alireza Badiei b, and assan heibani a a Department of Chemistry,
More informationSUPPLEMENTARY INFORMATION
Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using
More informationSupporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and
Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and
More informationSYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES
SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES 1 Ravibabu Velpula, 1 Ramesh Gondru, 2 Yashodhara Velivela and 1 Rajitha Bavantula* 1 Department of Chemistry, National
More informationSynthesis of Fused Heterocyclic Rings Incorporating Pyrrolo[2,1-b]benzothiazole Moiety
Article International Journal of Modern Organic Chemistry, 2012, 1(3): 193-202 International Journal of Modern Organic Chemistry Journal homepage: www.modernscientificpress.com/journals/ijorgchem.aspx
More informationCyanoacetanilides Intermediates in Heterocyclic Synthesis. Part 1: A Facile Synthesis of Polysubstituted and Condensed Pyridones
Journal of the Chinese Chemical Society, 2004, 51, 975-981 975 Cyanoacetanilides Intermediates in eterocyclic Synthesis. Part 1: A Facile Synthesis of Polysubstituted and Condensed Pyridones Y. A. Ammar,
More informationGLOBAL JOURNAL OF ENGINEERING SCIENCE AND RESEARCHES
GLOBAL JOURNAL OF ENGINEERING SCIENCE AND RESEARCHES NEW AND ONE POT-SYNTHESIS OF FUNCTIONALLY SUBSTITUTED PYRIDINES FROM ENAMINOKETONES Fathy Muhammad AbdelAziz El-Taweel *1, Hagar Hussein Nawwar 2 *1
More informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
More informationSynthesis and characterization of novel bis (α aminophosphonates) with terminal chromone moieties
General apers ARKIVC 2008 (ii) 71-79 Synthesis and characterization of novel bis (α aminophosphonates) with terminal chromone moieties Tarik El-Sayed Ali Department of Chemistry, Faculty of Education,
More information2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide
217 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide O O Cl NH 3 NH 2 C 9 H 7 ClO (166.6) (17.) C 9 H 9 NO (147.2) Classification Reaction types and substance classes reaction of
More informationChemistry of Pyrones, Part 5: New Crown Ether and Podand Derivatives of 3,5-Bis(bromomethyl)-2,6-diphenyl-4H-pyran- 4-one
Molecules 2001, 6, 721-727 molecules ISS 1420-3049 http://www.mdpi.org Chemistry of Pyrones, Part 5: ew Crown Ether and Podand Derivatives of 3,5-Bis(bromomethyl)-2,6-diphenyl-4H-pyran- 4-one Aziz Shahrisa*
More informationChia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization
More informationmolecules ISSN
Molecules 2005, 10, 1153-1160 molecules I 1420-3049 http://www.mdpi.org ynthesis of Thiadiazoles and 1,2,4-Triazoles Derived from yclopropane Dicarboxylic Acid. A. ussain K. harba*, Rida.Al-Bayati, adjet
More information3-Aryl-2-sulfanylpropenoic acids as precursors for some novel (Z)-5-substituted-2-alkoxy-2-trichloromethyl-4-thiazolidinones
3-Aryl-2-sulfanylpropenoic acids as precursors for some novel (Z)-5-substituted-2-alkoxy-2-trichloromethyl-4-thiazolidinones Nadia Hanafy Metwally Department of Chemistry, Faculty of Science, Cairo University,
More informationAn improved preparation of isatins from indoles
An improved preparation of isatins from indoles Jiro Tatsugi,* Tong Zhiwei, and Yasuji Izawa Department of Applied Chemistry, Faculty of Engineering, Aichi Institute of Technology, Yachigusa, Yakusa-cho,
More informationElectronic Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly
More informationEnaminones as building blocks in organic syntheses: on the reaction of 3-dimethylamino-2-propenones with malononitrile
General Papers AKIVC 2009 (xi) 1-10 Enaminones as building blocks in organic syntheses: on the reaction of 3-dimethylamino-2-propenones with malononitrile Saleh M. Al-Mousawi,* a Moustafa Sherief Moustafa,
More informationFigure S1 - Enzymatic titration of HNE and GS-HNE.
Figure S1 - Enzymatic titration of HNE and GS-HNE. Solutions of HNE and GS-HNE were titrated through their reduction to the corresponding alchools catalyzed by AR, monitoring the decrease in absorbance
More informationSupporting Information
Supporting Information Catalyst- and solvent-free one-pot synthesis of some novel polyheterocycles from aryldiazenyl salicylaldehyde derivatives Narsidas J. Parmar 1, Rikin A. Patel 1, Shashikant B. Teraiya
More informationKinetic Isotope Effects
1 Experiment 31 Kinetic Isotope Effects Isotopic substitution is a useful technique for the probing of reaction mechanisms. The change of an isotope may affect the reaction rate in a number of ways, providing
More informationSynthesis and Absorption Spectral Properties of Bis-methine Dyes Exemplified by 2,5-Bis-arylidene-1-dicyanomethylene-cyclopentanes
426 Bull. Korean Chem. Soc. 2003, Vol. 24, 4 Abdullah Mohamed Asiri Synthesis and Absorption Spectral Properties of Bis-methine s Exemplified by 2,5-Bis-arylidene-1-dicyanomethylene-cyclopentanes Abdullah
More informationJournal of Chemical and Pharmaceutical Research
Available on line www.jocpr.com Journal of Chemical and Pharmaceutical esearch J. Chem. Pharm. es., 2010, 2(2): 381-386 I o: 0975-7384 A convenient one pot synthesis of some novel benzothiazole and its
More informationIssue in Honor of Prof. Kjell Undheim ARKIVOC 2001 (x) 85-94
Heterocyclic synthesis with activated nitriles : an expeditus synthetic approach to polyfunctionally substituted pyrroles, heterocyclopyrimidines and coumarins Ayman W. Erian, a * Sherif M. Sherif a, and
More informationSupplementary Material. Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons
Supplementary Material Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons İrfan Çapan a and Süleyman Servi b a Gazi University, Technical Sciences
More informationA Route to Dicyanomethylene Pyridines and Substituted Benzonitriles Utilizing Malononitrile Dimer as a Precursor
Molecules 2011, 16, 298-306; doi:10.3390/molecules16010298 ticle PE ACCESS molecules ISS 1420-3049 www.mdpi.com/journal/molecules A Route to Dicyanomethylene Pyridines and Substituted Benzonitriles Utilizing
More informationThe Synthesis of Triphenylmethano. will synthesize Triphenylmethanol, a white crystalline aromatic
HEM 333L rganic hemistry Laboratory Revision 2.0 The Synthesis of Triphenylmethano ol In this laboratory exercise we will synthesize Triphenylmethanol, a white crystalline aromatic compound. Triphenylmethanol
More informationAn efficient condensation of 4-oxo-4H-benzopyran-3-carbaldehydes with 3-methyl-1-phenyl-1H-pyrazol-5 (4H)-one
General Papers ARKIVC 2005 (xiv) 82-86 An efficient condensation of 4-oxo-4H-benzopyran-3-carbaldehydes with 3-methyl-1-phenyl-1H-pyrazol-5 (4H)-one Balaji R. Madje, Santosh S. Shindalkar, Madhav. Ware,
More informationFacile Multistep Synthesis of Isotruxene and Isotruxenone
Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw
More informationSupporting Information
Supporting Information Antonio Palumbo Piccionello, Annalisa Guarcello, Silvestre Buscemi, icolò Vivona, and Andrea Pace* Dipartimento di Chimica Organica "E. Paternò", Università degli Studi di Palermo,
More information1,3-Oxazines and Related Compounds. XIII.1) Reaction of Acyl Meldrum's. Acids with Schiff Bases Giving 2,3-Disubstituted 5-Acy1-3,4,5,6-
1860 Vol. 35 (1987) Chem. Pharm. Bull. 35( 5 )1860-1870(1987). 1,3-Oxazines and Related Compounds. XIII.1) Reaction of Acyl Meldrum's Acids with Schiff Bases Giving 2,3-Disubstituted 5-Acy1-3,4,5,6- tetrahydro-2h-1,3-oxazine-4,6-diones
More informationSubstituent Effect on 66Ring-Chain Tautomerism of l12,3,4-tetrahydro-s-tetrazines
Journal f. prakt. Chemie. Band 333, Heft 1, 1991, S. 61-65 J. A. Barth, Leipzig Substituent Effect on 66Ring-Chain Tautomerism of l12,3,4-tetrahydro-s-tetrazines M. M. EL-ABADELAH*, A. Q. HUSSEIN Chemistry
More informationSupporting Information. Excited State Relaxation Dynamics of Model GFP Chromophore Analogs: Evidence for cis-trans isomerism
Supporting Information Excited State Relaxation Dynamics of Model GFP Chromophore Analogs: Evidence for cis-trans isomerism Shahnawaz Rafiq, 1 Basanta Kumar Rajbongshi, 1 isanth. air, Pratik Sen,* and
More informationSupporting Information
Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of
More informationThe interaction of 1,4-diketones with thiazyl chloride (N SCl)
Issue in Honor of Dr. Douglas Lloyd ARKIVC 2002 (iii) 90-94 The interaction of 1,4-diketones with thiazyl chloride ( S) Sean M. Laaman a, tto Meth-Cohn a, and Charles W. Rees a,b a Chemistry Department,
More informationSynthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
More informationSulfuric Acid-Catalyzed Conversion of Alkynes to Ketones in an Ionic Liquid Medium under Mild Reaction Conditions
Sulfuric Acid-Catalyzed Conversion of Alkynes to Ketones in an Ionic Liquid Medium under Mild Reaction Conditions Wing-Leung Wong, Kam-Piu Ho, Lawrence Yoon Suk Lee, Kin-Ming Lam, Zhong-Yuan Zhou, Tak
More informationSYNTHESIS OF 15 N-LABELED ISOMERS OF 5-NITRO-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE (NTO)
SYNTHESIS OF 15 N-LABELED ISOMERS OF 5-NITRO-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE (NTO) Jimmie C. Oxley, James L. Smith, Kirk E. Yeager Chemistry Department New Mexico Institute of Mining & Technology Socorro,
More informationSupporting Information
Supporting Information for Engineering of indole-based tethered biheterocyclic alkaloid meridianin into -carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
More informationMicrowave Irradiation Versus Conventional Method: Synthesis of some Novel 2-Substituted benzimidazole derivatives using Mannich Bases.
International Journal of ChemTech Research CODE( USA): IJCRGG ISS : 0974-4290 Vol.6, o.2, pp 1110-1114, April-June 2014 Microwave Irradiation Versus Conventional Method: Synthesis of some ovel 2-Substituted
More informationTerpenoids: Investigations in Santonin Chemistry
1 Experiment 8 Terpenoids: Investigations in Santonin Chemistry Santonin, (I) is a well-known sesquiterpenoid that has received much study in the past. Because it is a highly functionalized compound, and
More informationBabak Karimi* and Majid Vafaeezadeh
Electronic upplementary Material (EI) for RC Advances This journal is The Royal ociety of Chemistry 2013 BA-15 functionalized sulfonic acid confined hydrophobic and acidic ionic liquid: a highly efficient
More informationModified Methods for the Synthesis of Carbazole from Phenothiazine
Molecules 2001, 6, 668-672 molecules I 1420-3049 http://www.mdpi.org Modified Methods for the ynthesis of Carbazole from Phenothiazine R. Bryan Miller, *, teven C. Farmer Department of Chemistry, University
More informationSupporting Information
Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,
More informationSynthesis of oxo analogs of Lamotrigine and related compounds 1
General Papers ARKIVC 2003 (i) 22-28 Synthesis of oxo analogs of Lamotrigine and related compounds 1 Jan laváč, * Roman Buchtík, Jan Slouka, Pavel radil, and Iveta Wiedermannová Department of rganic Chemistry,
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationO-Allylation of phenols with allylic acetates in aqueous medium using a magnetically separable catalytic system
Supporting information for -Allylation of phenols with allylic acetates in aqueous medium using a magnetically separable catalytic system Amit Saha, John Leazer* and Rajender S. Varma* Sustainable Technology
More informationmolecules ISSN
Molecules 001, 6, 44-447 molecules ISSN 140-3049 http://www.mdpi.org Facile and Fast Pinacol Rearrangement by All 3 in the Solid State Parviz Rashidi-Ranjbar* and Ebrahim Kianmehr Department of hemistry
More informationMICROWAVE SYNTHESIS OF 1- CARBOXAMIDO-3, 5- DIARYL 2 -PYRAZOLINES
Int. J. Chem. Sci.: 6(1), 2008, 122-126 MICROWAVE SYTHESIS OF 1- CARBOXAMIDO-3, 5- DIARYL 2 -PYRAZOLIES P. R. BHAGAT Department of Chemistry, Jawaharlal Darda Institute of Engg. & Technology, Lohara, Amravati
More informationSupplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and
More informationExperiment 2 Solvent-free Aldol Condensation between 3,4-dimethoxybenzaldehyde and 1-indanone
Experiment 2 Solvent-free Aldol Condensation between 3,4-dimethoxybenzaldehyde and 1-indanone Chemical Concepts Carbonyl chemistry, base catalyzed aldol reaction, melting point, recrystallization Green
More informationSynthesis of 2,5,7-triamino[1,2,4]triazolo[1,5-a][1,3,5]triazines as potential antifolate agents
Anton V. Dolzhenko, Anna V. Dolzhenko and Wai-Keung Chui Synthesis of 2,5,7-triamino[1,2,4]triazolo[1,5-a][1,3,5]triazines as potential antifolate agents Department of Pharmacy, Faculty of Science, ational
More informationpyrazoles/isoxazoles library using ketene dithioacetals
Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals Mahesh M. Savant, Akshay M. Pansuriya, Chirag V. Bhuva, Naval Kapuriya, Anil S. Patel, Vipul B. Audichya,
More informationSupporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Supporting Information Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using
More informationEffect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
More informationSupporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles** Kohei Fuchibe, Masaki Takahashi,
More informationISATIN (PER-O-ACETYL- -D- GALACTOPYRANOSYL)THIOSEMICARBAZONES
ISATIN (PER--ACETYL- -D- GALACTPYRANSYL)THISEMICARBAZNES Nguyen Dinh Thanh*, Nguyen Thi Kim Giang Faculty of Chemistry, College of Science, Vietnam National University (Hanoi), 19 Le Thanh Tong, Hanoi
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
More informationExperiment 24. Chemical recycling of poly(ethylene) terephthalate (PET)
Methods of pollution control and waste management Experiment 24 Chemical recycling of poly(ethylene) terephthalate (PET) Manual Department of Chemical Technology The aim of this experiment is to gain knowledge
More informationSupporting Information. (1S,8aS)-octahydroindolizidin-1-ol.
SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.
More informationGeneral Papers ARKIVOC 2007 (xvi) 65-72
Reaction of α,α-dibromoketones with 4-amino-5-mercapto-3-methyls-triazole: synthesis of some 7H-7-alkoxy-6-aryl-3-methyl-s-triazolo [3,4-b][1,3,4]thiadiazines m Prakash,* and isha harma Department of Chemistry,
More informationMaharashtra, India. Departments of Chemistry, R.C.Patel ASC College, Shirpur , Maharashtra, India
International Journal of ChemTech Research CODEN (USA): IJCRGG, ISSN: 0974-4290, ISSN(Online):2455-9555 Vol.10 No.7, pp 249-253, 2017 Microwave Assisted Synthesis of 3,4-bis (Substituted Phenyl) -7-(4-Methyl
More informationMaksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov
1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv
More informationSyntheses and Biological Activities of 6-Aryl-3-(3-hydroxypropyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines
, 297-303 Full Paper molecules ISS 1420-3049 http://www.mdpi.org Syntheses and Biological Activities of 6-Aryl-3-(3-hydroxypropyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines Jian-yu Jin 1, Li-xue Zhang
More informationAppendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Appendix A Supplementary Information Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
More informationSupporting Information
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 A rare case of a dye co-crystal showing better dyeing performance Hui-Fen Qian, Yin-Ge Wang,
More informationSupporting information for Bulk nanostructure of the prototypical good and poor
Electronic Supplementary Material (ESI) for Physical hemistry hemical Physics. This journal is the wner Societies 06 Supporting information for Bulk nanostructure of the prototypical good and poor solvate
More informationSBA-15-functionalized sulfonic acid confined acidic ionic liquid: a powerful and water-tolerant catalyst for solvent-free esterifications
SBA-15-functionalized sulfonic acid confined acidic ionic liquid: a powerful and water-tolerant catalyst for solvent-free esterifications Babak Karimi* a, Majid Vafaeezadeh a a Department of Chemistry,
More informationmolecules ISSN
Molecules 2005, 10, 1318 1324 molecules ISS 1420-3049 http://www.mdpi.org Synthesis of ew Potentially Bioactive Bicyclic 2-Pyridones Maxime D. Crozet 1, Pascal George 2, Michel P. Crozet 1 and Patrice
More informationSynthesis and Characterization of 9-Phenyl-9H-purin-6-amines from 5-Amino-1-phenyl- 1H-imidazole-4-carbonitriles
ISS: 09734945; CODE ECJAO E Chemistry http://www.ejournals.net Vol. 4, o. 3, pp. 372375, July 2007 Synthesis and Characterization of 9Phenyl9purin6amines from 5Amino1phenyl 1imidazole4carbonitriles ASIE
More informationSupporting Information
Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy
More informationSUPPORTING INFORMATION. in the Synthesis of Fluorenones and ortho-arylated. Benzonitriles
SUPPRTING INFRMATIN Carbon-Hydrogen Bond Functionalization Approach in the Synthesis of Fluorenones and ortho-arylated Benzonitriles Dmitry Shabashov, Jesús R. Molina Maldonado and lafs Daugulis* Department
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Amino and itro Substituted 2-Amino-1H-benzo[de]isoquinoline-
More informationMultistep Synthesis of 5-isopropyl-1,3-cyclohexanedione
Multistep Synthesis of 5-isopropyl-1,3-cyclohexanedione The purpose of this experiment was to synthesize 5-isopropyl-1,3-cyclohexanedione from commercially available compounds. To do this, acetone and
More informationSupporting Information
Supporting Information An Alternative Approach to Synthesis of 3-(4-chloro butyl)-1h-indole -5-carbonitrile: A key intermediate of Vilazodone hydrochloride, an antidepressant drug Anitha N, Sudhakar Reddy
More informationSUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
More informationFluorescence Studies of Selected 2-Alkylaminopyrimidines
Molecules 2004, 9, 520-526 molecules ISS 1420-3049 http://www.mdpi.org Fluorescence Studies of Selected 2-Alkylaminopyrimidines Z. Abdullah 1, *,. Mohd Tahir 2, M. R Abas 1, Z. Aiyub 1 and B.K Low 3 1
More information*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3h)-one catalyzed by Graphene Oxide
More informationPreparation of some light-sensitive 2-nitrophenyl-2,3-dihydro-1H-benzodiazepines
Preparation of some light-sensitive 2-nitrophenyl-2,3-dihydro-1H-benzodiazepines Ricaurte Rodríguez,* a Braulio Insuasty, b Rodrigo Abonía, and Jairo Quiroga b a Universidad Nacional de Colombia, Department
More informationDivergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site
More informationSupporting Information
1 A regiodivergent synthesis of ring A C-prenyl flavones Alberto Minassi, Anna Giana, Abdellah Ech-Chahad and Giovanni Appendino* Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
More informationSupporting Information. Novel route for the synthesis of 5-substituted 1-H tetrazoles in presence of polymer-supported palladium nanoparticles
Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2017 Supporting Information ovel
More informationEnantioselective Synthesis of Fused Heterocycles with Contiguous Stereogenic Centers by Chiral Phosphoric Acid-Catalyzed Symmetry Breaking
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Enantioselective Synthesis of Fused Heterocycles with Contiguous Stereogenic Centers by Chiral
More informationSynthesis and spectral characterization of related compounds of riluzole, an amyotrophic lateral sclerosis drug substance
ynthesis and spectral characterization of related compounds of riluzole, an amyotrophic lateral sclerosis drug substance Bollikonda atyanarayana,* M. aravanan, K. iva Kumari, D. P. Lokamaheshwari, Ch.
More information