RESEARCH ARTICLE ISSN Synthesis of Chalcones by grindstone chemistry as an intermediate in Organic Synthesis

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1 IT J CURR SCI 2014, 13: E RESEARCH ARTICLE ISS Synthesis of Chalcones by grindstone chemistry as an intermediate in rganic Synthesis Abstract Pravina B. Piste PG Department of Chemistry, Y.C. Institute of Science, Satara (MH), India *Corresponding author: ppiste321@gmail.com A facile synthesis of some novel 4-(Sub Phenyl)-1-phenyl 2-propen-1-ones (I-IX) has been achieved by the condensation of omatic and aliphatic ketone with various substituted aromatic aldehydes through intramolecular aldol condensation using solid ah by using grinding technique. All synthesized compounds were characterized on the basis of IR, MR and UV spectroscopic data and elemental analysis. Keywords: Chalcones, Aldol condensation, Grindstone Chemistry Received: 05 th June; Revised: 17 th July; Accepted: 25 th September; IJCS ew Liberty Group 2014 Introduction The chalcones and their derivatives are important intermediates in organic synthesis. They serve as starting material for the synthesis of variety of heterocyclic compounds which are of physiological importance. Due to the presence of enone functionality in chalcone moiety confers wide range of biological applications such as antibacterial (pletalova, 2000), antifungal (Go et al., 2005), antitumor (Ducki et al., 1998), antiulsar (Kyogoku et al., 1979), anticancer (Konieczny et al., 2007), analgesic (Viana et al., 2003), antiimflammatory (Jin et al., 2007), antileishmanial (arender et al., 2005) etc. The utility of chalcones due to their usefulness as in synthesis of various heterocyclic compounds. Solid-state reaction occurs more targets and more importantly they have been extensively employed as intermediates in the synthesis of heterocyclic and carbocyclic systems as per Scheme-II. Materials and Methods All chemicals were of synthetic grade (S. D. Fine Chem. Ltd. Mumbai, India). The melting points were recorded on electro-thermal apparatus and are uncorrected. The purity of the compounds was checked by TLC on precoated Si 2 gel (HF254, 200 mesh) aluminium plates (E Merk) using hexane and ethyl acatate visualized in iodine chamber. IR spectra were recorded in KBr on a perkin- Elmer model HMR spectrum recorded on Varian Mercury 300 MHz instrument using CDCl 3, DMS-d6 as solvent (chemical shift in δ ppm), using TMS as internal efficiently and more selectively than does the solution standard. UV spectra were recorded in ethanol on reaction, since molecules in the crystal are arranged tightly and regularly. Reaction are simple to handle, reduce pollution, comparatively cheaper to operate and may be regarded as more economical and ecologically favorable procedure in chemistry. In the present investigation, grindstone technique was used for the synthesis of titled compounds. All these facts make them desired synthetic Beckmann DK-1 spectrophotometer. Elemental analysis was performed on a Heracus CH analyzer and was within the ±0.5% of the theoretical values. Synthesis of 4-(Sub Phenyl)-1-phenyl 2-propen-1-one ( I-IX ) Different aldehydes (0.05 mmol), substituted acetophenone (0.05 mmol) and 2.0 g solid ah is taken in a small mortar. Grinded the mixture thoroughly for 5-10

2 Scheme-I R Solid ah H + Grinding Scheme-II H Pyrazolin (ii) (i) Pyrazole H 2 (iii) (vi) H 2 S xazine (iv) (v) Thiazine (vii) H Pyrimidine H Pyrazole Ph Isoxazole (i) Hydrazine/EtH (ii) H 2.H 2 /GAA (iii) =C(H 2 ) 2,EtH/aH (iv) S=C(H 2 ) 2,EtH/aH (v) H 2 H.HCl,EtH (vi) =C(H 2 ) 2 (Vii) Ph.H.H 2 /GAA Table 1. Physical data of synthesized compounds (I-IX) R R1 bserved M.P.( 0 C) Physical Constant Literature M.P.( 0 C) %Yield m-,p-di-h -C 6 H C 6 H 5 -C 6 H p-h -C 6 H o-h,p-ch 3 -C 6 H p-ch 3 -CH p-(ch 3 ) 2 -CH m,p-di-h -CH C 6 H 5 -CH p-ch 3 -C 6 H

3 Fig.1. The color and nature of synthesized compounds (I-IX) Compound o.i Compound o.ii Compound o.iii Compound o.-iv Compound o.-v Compound o.-vi Compound o.-vii Compound o.-viii Compound o.-ix Table 2. Spectral and elemental analysis of synthesized compounds (I-IX) Compound o. Spectral analysis I UV (λmax): 312 nm.;ir (KBr),Ѵmax: -H(3465), >C=(1658), >C=C<(1622) cm -1.; 1 H MR ( CDCl 3 ),δ: (1H, d,=ch-), (8H, m, -H),6.81(1H, d, -C-CH=), 4.9 (1H, s, C-4 -H) 9 ppm. II UV (λmax): 306 nm.;ir (KBr),Ѵmax: >C=(1660), >C=C<(1638 ) cm -1.; 1 H MR( CDCl 3 ),δ: δ: (1H, d,=ch-), (10 H, m, -H), 6.81 (1H, d, -C-CH=) ppm. III UV (λmax): 312 nm.;ir (KBr),Ѵmax: -H(3465), >C= (1662), >C=C<(1622) cm -1.; 1 H MR( CDCl 3 ),δ: (1H, d,=ch-), (9H, m, -H), 6.81 (1H, d, -C-CH=), 4.89 (1H, s, C-4 -H) ppm. IV UV (λmax): 308 nm.;ir (KBr),Ѵmax: -H(3483), >C=(1665), >C=C<(1620) cm -1.; 1 H MR( CDCl 3 ),δ: (1H, d,=ch-), (8H, m, -H), 6.81 (1H, d, -C-CH=), 5.09 (1H, s, C-2 -H),3.54( 3H,s,-CH 3 ) ppm. V UV (λmax): 339 nm.;ir (KBr),Ѵmax: >C=(1678), >C=C<(1622) cm - 1.; 1 H MR( CDCl 3 ),δ: (1H, d,=ch-), (4H, m, -H), 6.81 (1H, d, -C-CH=),3,83( 3H,s,-CH 3 ), 2.54(3H,s,-CCH 3 ) ppm. VI UV (λmax): 308 nm.;ir (KBr),Ѵmax: -H(3465), >C=(1660), >C=C<(1622) cm -1.; 1 H MR( CDCl 3 ), δ: (1H, d,=ch-), (4H, m, -H), 6.81 (1H, d, -C-CH=),3.26( 6H,s,-CH 3 ), 2.54(3H,s,-CCH 3 ) ppm. Elemental analysis Calc./ (Found) % C H (74.92) (86.50) (80.35) (75.60) (75.00) (76.15) 5.00 (4.99) 5.77 (5.78) 5.36 (5.30) ) 6.82 (6,79) 7.93 (7.91) (7.40)

4 VII UV (λmax): 313 nm.;ir (KBr),Ѵmax: -H(3470), >C=(1660), >C=C<(1622),C- (1280) cm H MR( CDCl 3 ),δ: (1H, d,=ch-), (3H, m, -H), 6.81 (1H, d, -C-CH=), 4.9 (1H, s, C-4 -H), 2.43( 3H,s,-CH 3 ) ppm VIII UV (λmax): 307 nm.;ir (KBr),Ѵmax:>C=(1660), >C=C<(1622) cm - 1.; 1 H MR( CDCl 3 ),δ: (1H, d,=ch-), (5H, m, -H), 6.81 (1H, d, -C-CH=), 2.43( 3H,s,-CH 3 ) ppm. IX UV (λmax): 313 nm.;ir (KBr),Ѵmax: >C=(1659), >C=C<(1622), C- (1275) cm H MR ( CDCl 3 ), δ: (1H, d,=ch-), (9H, m, -H), 6.81 (1H, d, -C-CH=), 2.83( 3H,s,-CH 3 ) ppm (67.38) (82.16) (80.65) ) 6.85 (6.81) 5.88 (5.85) mins. The mixture become solid, yellow in color and kept it overnight. Then washed with cold water and filtered to obtain the crude product. Recrystallize product by using the solvent as an ethanol, dried and weight. Results and Discussion We have developed efficient, operationally simple, environmental benign method under solvent free condition (solid ah) by using grindstone chemistry. Many researches have been done on synthesis of Chalcone by using different methods such as Conventional and nonconventional methods which requires larger time and less atom economy. But our method is differing from all these methods as it requires shorter reaction time and high yields up to 75 to 85%. Chalcone is a versatile molecule which having wide range of biological and pharmacological applications as described. Due to its utility we have synthesized chalcones by grinding technique which is very fertile and easiest to all researchers. Main object in synthesis of chalcone is that it can be further used in synthesis of heterocyclic compounds i.e. it acts as an intermediates as per Scheme-II further we have examined the synthesized compounds by using analytical techniques as per Table-I and II. The nature and colour of corresponding compounds as shown below: Conclusion We have developed a simple, efficient and more eco-friendly method for synthesis of chalcones under solvent free condition by grinding technique. The notable advantages of present method are no organic solvent required (except for the product recrystallisation), waste minimization, simple operation, clean reaction profile, easy work-up, shorter reaction time (4-8 min), high yields (75-85%) and eco-friendly as compared to conventional method. Acknowledgement Author thanks to the Department of Chemistry for providing research facilities and ational Chemical Laboratory, Pune, India for their spectral interpretation. References pletalova V (2000). Chalcones and their heterocyclic analogues as potential therapeutic agents of bacterial diseases. Ceska Slov Farm 49: Go ML, Wu X, Liu, XL (2005). Chalcones: an update on cytotoxic and chemoprotective properties. Curr Med Chem 12: 483. Ducki S, Forrest R, Hadfield JA, Kendall A, Lawrence J, Mc-Gown, AT, Rennison D (1998). Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem 8: Kyogoku K. Hatayama S, Yokomori R, Saziki S, akane M, Sasajima J, Sawada M, Tanaka I (1979). Chem Pharm Bull 27(12): Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakiec R, Augusttynowiczkopec E, Zwolska Z

5 (2007). Synthesis of isomeric, oxathiolone fused chalcones and comparison, their activity towards various microorganisms and human cancer cell lines. Chemical and Pharmaceutical Bulletin 55: Viana GS, Bandeira MA, Mantos FJ (2003). Analgesic and antiinflammatory effects of chalcones isolated from Myracrodruon urundeuva allemão. Phytomedicine 10: 189. Jin F, Jin YL, Sohn DW, Kim SA, Sohn DH, Kim YC, Kim HS (2007). Structural requirements of 2,4,6 - Tris (methoxymethoxy) chalcones derivatives for anti-inflammatory activity. chives of Pharmacal Research 30: arender T, Khaliq T, Shewata, ishi, Goyal, Gupta S (2005). Synthesis of chromenchalcones and evaluation of their in vitro antileishmanial activity. Bioorganic and Medicinal Chemistry 13: Ameta KL, itu SR, Biresh K (2011). Synthesis of some novel chalcones and their facile one-pot conversion to 2-aminobenzene-1, 3-dicarbonitriles using malononitriles. Analele Universităţii din Bucuresti- Chimie (serie nouă) 20(1):