*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3
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1 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 nanosheets in aqueous medium: on-water synthesis accompanied by carbocatalysis and selective C-C bond cleavage Nazia Kausar a, Indranil Roy b, Dipankar Chattopadhyay b, Asish R. Das a * Department of Chemistry, University of Calcutta, Kolkata , India b Department of Polymer Science and Technology, University of Calcutta, 92 A.P.C. Road, Kolkata , India. *Corresponding author. Tel.: , ; fax: ; address: ardchem@caluniv.ac.in, ardas66@rediffmail.com (A R Das) Content Page Numbers Materials and Method 2 Preparation of GO nanosheets 3 General Procedure for the synthesis of 2,3-dihydroquinazolinone 3 General Procedure for the synthesis of quinazolin-4(3h)-one 3-4 Physical Characterization data of the synthesized compounds HNMR & 13 CNMR and HRMS Spectra of the synthesized compounds
2 Materials and Methods 1 H-NMR and 13 C-NMR spectral analysis were carried out on Bruker-Advance Digital 300 MHz and 75 MHz instruments where tetramethylsilane (TMS) was used as internal standard. Infrared spectra were recorded in KBr pallets in reflection mode on a Perkin Elmer RX-1 FTIR spectrophotometer. Suitable single crystal of compound 3h, 5a and 5j was mounted on a Bruker-AXS SMART APEX II diffractometer equipped with a graphite monochromator. All the reactions were monitored by thin layer chromatography carried out on Merck aluminum-blocked silica gel plates coated with silica gel G under UV light and also by exposure to iodine vapor for detection. Melting points were recorded on a Köfler Block apparatus. Synthetic grade chemicals from Sigma-Aldrich, Spectrochem and E-Merck were used for carrying out the organic reactions. 2
3 Preparation of GO Natural graphite powder is used for the synthesis of GO nanosheets. Graphite powder (1000 mg) and NaNO 3 (1000 mg) were added to 35ml of concentrated H 2 SO 4 (98%) under vigorous stirring in a 250 ml conical flask placed in an ice bath. The whole mass was converted to black slurry (it takes 2 min), then KMnO 4 (5000 mg) was added slowly to the slurry maintaining the reaction temperature between 15 o C and 20 o C. After 3 h, the entire system was taken out of the ice bath and diluted with 100 ml water and then further stirred for 3 h at ambient temperature. 200 ml hot water was added to the above reaction mixture followed by 30% H 2 O 2 until the excess permanganate and manganese dioxide had been reduced to colourless soluble manganese sulfate. The resultant yellow precipitate was washed with distilled water several times and then was subjected to centrifuge to get the pure graphene oxide powder. After repeated centrifugation, salts and ions results from the oxidation process can be removed from GO suspensions. The GO nanosheets sample was collected and dried at 60 o C for 24 h. The GO nanosheets were characterized using XRD, FTIR, FESEM and TEM images. General Procedure for the synthesis of 2, 3-dihydroquinazolinones: Anthranilamide (1 mmol) was added to aldehyde/ketone derivative (1 mmol) in aqueous medium (3 ml water) followed by GO nanosheets (25 mg) at room temperature. The mixture was then stirred for the required period of time (indicated by TLC). After completion of each reaction, product and the catalysts separated from reaction system by simple filtration. The crude product was then dissolved in EtOH (3 ml) and this allows separation of minute quantity of the catalyst through filtration and crystallization of the crude product from EtOH furnished pure compound. All compounds were well characterized by 1 H, 13 C NMR and FT-IR analysis. 3
4 General Procedure for the synthesis of quinazolin-4(3h)-one: a) Anthanilamide (1 mmol) was added to aldehyde/ketone derivative (1 mmol) in aqueous medium (3 ml water) followed by GO nanosheets (25 mg) and oxone (307 mg) at room temperature. The mixture was then stirred for the required period of time (indicated by TLC). After completion of each reaction, crude product was separated from reaction system by simple filtration. The crude product was then dissolved in EtOH (3 ml) and filtered. Finally crystallization of the crude product from EtOH offered the pure compound. All compounds were well characterized by 1 H, 13 C NMR and FT-IR analysis. b) Anthanilamide (1 mmol) was added to 1,3-diketones derivative (1 mmol) in aqueous medium (3 ml water) followed by GO nanosheets (25 mg) at 60 o C. The mixture was then stirred for the required period of time (indicated by TLC). After completion of each reaction, the crude product mixture was extracted with ethyl acetate (2x3ml) and finally purified by column chromatography (eluent- ethyl acetate/petroleum ether: 1:4). All compounds were well characterized by 1 H, 13 C NMR and FT-IR analysis. 4
5 2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3a) Yield: 94%, (0.211 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 5.79 (s, 1H), 5.87 (s, 1H), 6.6 (d, 1H, J=7.8 Hz), 6.88 (t, 1H, J= 7.5 Hz), (m, 1H), (m, 3H), (m, 2H), 7.9 (dd, 1H, J= 7.8 Hz, J= 1.5 Hz) ; 13 C NMR (75 MHz, CDCl 3 ): δ 89.0,124.7, 127.6, 127.7, 128.6, 128.7, 129.1, 131.2, 131.3, 133.4, 133.5, 139.3, 144.5, ; IR (KBr) cm -1 : 1615, 1659, 2925, 3061, 3186, (m-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3b) Yield: 92%, (0.219 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-d 6 ): δ 2.32 (s, 3H), 5.72 (s, 1H), (m, 2H), 7.08 (s, 1H), (m, 5H), 7.6 (d, 1H, J= 6.9 Hz), 8.26 (s, 1H); 13 C NMR (75 MHz, DMSO-d 6 ): δ 21.5, 67.00, 114.8, 117.5, 124.4, 127.7, 127.9, 128.6, 129.5, 133.7, 137.8,141.9, 148.3, 164.0; IR (KBr) cm -1 : 1610, 1655, 2920, 3063, 3185,
6 2-(3-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one (3c) Yield: 96%, (0.258 g); M.p C; Characteristics: Yellow crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), 5.82 (s, 1H), 6.65 (t, 2H,, J=8.1 Hz), (m, 1H), (m, 1H), (m, 2H), 8.1 (d, 2H, J=6.9 Hz); 13 C NMR (75 MHz, DMSO-D 6 ): δ 82.6, 114.9, 117.9, 127.6, 127.8, 128.8, 130.3, 130.9, 132.4, 133.9, 141.0, 147.8, 163.9; HRMS (ESI-TOF) m/z Calculated for [C 14 H 11 N 3 O 3 +Na] + : , found: ; IR (KBr) cm -1 : 1345, 1461, 1520, 1608, 1647, 2855, 2922, 3032, 3174, (2-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one (3d) Yield: 95%, (0.236 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 6.13 (s, 1H), 6.36 (s, 1H), 6.67 (d, 1H, J= 8.1 Hz), 6.89 (t, 1H, J= 7.5Hz), (m, 4H), (m, 1H), 7.93 (d, 1H, J= 7.5 Hz) ; 13 C NMR (75 MHz, CDCl 3 ): δ 66.2, 114.9, 115.4, 117.7, 127.8, 128.8, 129.2, 133.4, 133.9, 141.1, 148.1, 163.9; IR (KBr) cm -1 : 1618, 1650, 2922, 3051, 3176,
7 2-(4-bromophenyl)-2,3-dihydroquinazolin-4(1H)-one (3e) Yield: 95%, (0.287 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 5.74 (s, 1H), 6.02 (s, 1H), (m, 2H), (m, 6H), 7.74 (s, 1H) ; 13 C NMR (75 MHz, CDCl 3 ): δ 66.3, 114.9, 115.5, 117.8, 127.8, 128.8, 129.2, 133.4, 133.9, 141.2, 148.1, 163.9; IR (KBr) cm -1 : 16012, 1662, 2932, 3062, 3180, (4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one (3f) Yield: 95%, (0.245 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 5,82 (s, 1H), 5.90(s, 1H), 6.69 (d, 1H, J= 8.1 Hz), 6.92 (t, 1H, J= 7.7 Hz) (m, 2H), 7.43 (d, 2H, J= 8.4 Hz), 7.55 (d, 2H, J= 8.4 Hz), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ): δ 66.2, 114.9, 115.4, 117.7, 127.8, 128.8, 129.2, 133.4, 133.9, 141.1, 148.1, ; IR (KBr) cm -1 : 1607, 1658, 2927, 3060, 3188,
8 2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (3g) Yield: 92%, (0.219 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 2.39 (s, 3H), 5.78 (s, 1H), 5.87 (s, 1H), 6.67 (d, 1H, J= 8.1Hz), 6.90 (t, 1H, J= 7.5Hz), (m, 5H), 7.95 (d, 1H, J= 7.8Hz) ; 13 C NMR (75 MHz, CDCl 3 ): δ 21.4, 67.10, 114.8, 117.5, 124.4, 127.7, 127.9, 128.6, 129.5, 133.7, 137.8,141.9, 148.3, 154.1, 164.1; IR (KBr) cm -1 : 1512, 1607, 1660, 1908, 2855, 2924, 3060, 3189, (4-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one (3h) Yield: 97%, (0.261 g); M.p C; Characteristics: Yellow crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 6.05 (s, 1H), 6.09 (s, 1H) 6.71 (d, 1H, J= 7.8 Hz), 6.94 (t, 1H, J= 7.5Hz), 7.37 (t, 1H, J= 7.8Hz), 7.79 (d, 2H, J= 8.1 Hz), 7.94 (d, 1H, J= 7.8 Hz), 8.30 (d, 2H, J= 7.8 Hz) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 79.9, 114.9, 117.9, 127.6, 127.8, 128.8, 130.3, 130.9, 132.4, 133.9, 141.0, 147.7, 163.9; IR (KBr) cm -1 : 1525, 1615, 1643, 2856, 2923, 3030, 3179,
9 2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3i) Yield: 88%, (0.211g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 4,43 (s, 1H), 5.78 (s, 1H), 5.86 (s, 1H), 6.67(d, 1H, J=8.1 Hz), 6.90 (t, 1H, J=7.5 Hz), (m, 5H), 7.95 (d, 1H, J=7.8 Hz), 8.33 (s, 1H) ; 13 C NMR (75 MHz, DMSO-d 6 ): δ 66.8, 114.0, 114.8, 115.5, 117.5, 127.7, 128.6, 133.7, 133.9, , 164.1; IR (KBr) cm -1 : 1622, 1655, 2930, 3062, 3179, 3302, (4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3j) Yield: 89%, (0.226 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ 3.77 (s, 3H), 5.72 (s, 1H), (m, 2H), (m, 6H), 7.61 (d, 1H, J=6.9 Hz) 8.26 (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 55.6, 66.7, 114.0, 114.8, 115.4, 117.5, 127.7, 128.6, 133.6, 133.9, , 164.1; IR (KBr) cm -1 : 1473, 1599, 1676, 2923, 3183, 3315,
10 2-(2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3k) Yield: 89%, (0.214 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 4.61 (s, 1H), 5.92 (s, 1H), 5.98 (s, 1H), (m, 4H), 6.77 (d, 1H, J=7.8 Hz), 7.02 (d, 1H, J=7.5 Hz), (m, 2H), 8.91 (s, 1H); 13 C NMR (75 MHz, DMSO-D 6 ): δ 69.9, 128.4, 128.5, 128.6, 129.0, 132.1, 132.7, 133.9, 135.8, 140.5, 156.7, ; IR (KBr) cm -1 : 1618, 1663, 2932, 3056, 3176, 3306, (thiophen-2-yl)-2,3-dihydroquinazolin-4(1H)-one (3l) Yield: 90%, (0.207 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 5.95 (s, 1H), 6.21 (s, 1H), 6.71 (d, 1H, J=7.5 Hz), 6.93 (t, 1H, J=8.1 Hz), (m, 1H), (m, 3H), 7.95 (d, 1H, J=5.7) ; 13 C NMR (75 MHz, CDCl 3 ): δ 62.1, 112.9, 113.9, 121.0,126.5, 126.7, 127.6, 134.9, 143.4, 145.4, 146.2, 160.0; IR (KBr) cm -1 : 1376, 1457, 1651, 1763, 2853, 2923,
11 2-isopropyl-2,3-dihydroquinazolin-4(1H)-one (3m) Yield: 88%, (0.167 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 0.93 (d, 6H, J=6.9 Hz), 1.89 (m, 1H), 4,59 (d, 1H, J=6.9 Hz), (m, 4H), 7.18 (s. 1H), 7.74 (s, 1H); 13 C NMR (75 MHz, DMSO-D 6 ): δ 16.9, 17.3, 33.2, 69.6, 114.5, 115.1, 116.9, 127.6, 133.4, 148.9, 164.3; IR (KBr) cm -1 : 1372, 1457, 1656, 1763, 2853, 2923, 3206, (2-hydroxy-4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3n) Yield: 87%, (0.235 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ 3.72 (s, 3H), 4.92 (s, 1H), 5.42 (s, 1H), 5.94 (s, 1H), (m, 3H), (m, 2H), 7.19 (t, 1H, J=7.2 Hz), 7.53 (d, 1H, J=7.5 Hz) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 55.7, 66.8, 114.0, 114.8, 115.4, 117.5, 127.7, 128.6, 133.6, 133.9, , 164.2; IR (KBr) cm -1 : 1473, 1592, 1676, 2937, 3182, 3312, 3320, (4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)benzonitrile (3o) 11
12 Yield: 92%, (0.229 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): 5.78 (s, 1H), 5.86 (s, 1H), 6.67 (d, 1H, J=8.1 Hz), 6.90 (t, 1H, J=7.5 Hz), (m, 6H), 8.49 (s, 1H) ; 13 C NMR (75 MHz, DMS)-d 6 ): δ 76.9, 114.9, 118.1, 127.6, 127.8, 128.8, 130.3, 130.9, 132.4, 133.9, 141.1, 147.7, ; IR (KBr) cm -1 : 1475, 1595, 1676, 2208, 2923, 3180, 3316, (furan-2-yl)-2,3-dihydroquinazolin-4(1H)-one (3p) Yield: 90%, (0.193 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 5.76 (s, 1H), 6.72 (s, 1H), (m, 3H), 7.61 (s, 1H), 7.73 (d, 2H, J=6.9 Hz), 8.24 (d, 2H, J=6.9 Hz) ; 13 C NMR (75 MHz, CDCl 3 ): δ 60.0, 112.9, 113.9, 121.0, 126.5, 126.7, 127.6, 134.9, 143.4, 145.4, 146.2, 149.2; IR (KBr) cm -1 : 1673, 2928, 3174, 3309, (2,3-dichlorophenyl)-2,3-dihydroquinazolin-4(1H)-one (3q) 12
13 Yield: 94%, (0.274g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 6.16 (s, 1H), (m, 2H), (m, 2H), 7.35 (dd, 1H, J=8.1 Hz, J=1.5 Hz), 7.44 (s, 1H), (m, 2H), 7.68 (dd, 1H, J=7.9 Hz, J=1.5 Hz) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 64.7, 114.9, 117.9, 127.6, 127.8, 128.8, 130.3, 130.9, 132.4, 133.9, 141.1, 147.7, ; IR (KBr) cm -1 : 1618, 1656, 2922, 3178, 3311, octyl-2,3-dihydroquinazolin-4(1H)-one (3r) Yield: 85%, (0.221g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 0.92 (t, 3H, J=6.9 Hz ), (m, 14H), 6.00 (s, 1H), 6.73 (t, 1H, J=7.5 Hz), (m, 3H), 8.49 (s, 1H); 13 C NMR (75 MHz, CDCl 3 ): δ 16.9, 17.3, 23.9, 26.2, 29.6, 33.2, 69.9, 114.5, 115.1, 116.9, 127.6, 133.4, 148.9, 164.3; IR (KBr) cm -1 : 1617, 2928, 3174, 3309, (2,3-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3s) Yield: 89%, (0.253 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ 3.75 (s, 6H), 5.94 (s. 1H), (m, 3H), 6.98 (s, 1H), 7.16 (t, 2H, J=7.5 Hz), 7.53 (d, 2H, J=7.5 Hz), 7.9 (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 56.2, 61.1, 61.6, 13
14 113.4, 114.8, 115.1, 117.4, 119.5, 124.3, 127.7, 133.6, 134.9, 146.5, 148.4, 152.7, 164.1; IR (KBr) cm -1 : 1622, 2924, 3170, 3319, methyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (5a) Yield: 86%, (0.205 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ 1.63 (s, 3H), 6.55 (t, 1H, J=7.5 Hz ), 6.76 (d, 1H, J=8.1 Hz), 7.19 (d, 1H, J=7.2 Hz), 7.28 (t, 2H, J=7.2 Hz), (m, 3H), 7.66 (s, 1H), 8.79 (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 31.1, 70.5, 114.7, 115.4, 117.2, 125.6, 127.4, 127.6, 128.3, 133.7, 147.6, 148.1, 164.2; IR (KBr) cm -1 : 1622, 1477, 1658, 2933, 3060, 3181, ethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one (5b) Yield: 85%, (0.162 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 0.97 (t, 3H, J=6.5 Hz ), 1.42 (s, 3H), 1.73 (q, 2H, J=7.5 Hz ), 6.37 (s, 1H), 6.54 (d, 1H, J=8.1 Hz ), 6.73 (t, 1H, J=7.5 Hz ), (m, 2H), 7.79 (d, 1H, J=6.6 Hz); 13 C NMR (75 MHz, CDCl 3 ): δ 8.1, 27.5, 34.8, 70.1, 114.4, 118.5, 128.3, 133.9, 160.6; IR (KBr) cm -1 : 1612, 1489, 1653, 2925, 3186, isopropyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one (5c) 14
15 Yield: 89%, (0.182 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 0.81 (d, 6H, J=6.6 Hz), 1.29 (s, 3H), (m, 1H), (m, 2H), (m,1h), 7.47 (t, 1H, J=6.8 Hz), 7.78 (s, 1H), 7.83 (s, 1H) ; 13 C NMR (75 MHz, CDCl 3 ): δ 18.9, 27.5, 34.8, 70.1, 114.5, 118.5, 128.3, 133.9, 143.8, 160.6; IR (KBr) cm -1 : 1610, 1485, 1513, 1658, 2931, 3186, (2-hydroxyphenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one (5d) Yield: 84%, (0.213 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 1.35 (s, 3H), (m, 4H), 7.09 (t, 1H, J=7.7 Hz), 7.20 (t, 1H, J=7.5 Hz), (m, 2H), 7.68 (s, 1H), 7.90 (s, 1H) ; 13 C NMR (75 MHz, CDCl 3 ): δ 24.1, 70.5, 114.7, 115.4, 117.2, 125.6, 127.4, 127.6, 128.3, 133.7, 147.6, 148.1, 164.3; IR (KBr) cm -1 : 1616, 1482, 1518, 1656, 2929, 3060, 3187, 3310, methyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one (5e) 15
16 Yield: 83%, (0.209 g); M.p ; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 1.78 (s, 3H), 2,38 (s, 3H), (m, 2H), 6.89 (s, 1H), 7.03 (d, 1H, J=7.5 Hz), (m, 2H), 7.34 (d, 2H, J=8.4 Hz), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ): δ 21.4, 29.5, 70.6, 114.5, 114.6, , 118.8, 125.0, 128.2, 129.0, 133.8, 137.7, 141.9, 145.6, 164.5; IR (KBr) cm -1 : 1612, 1482, 1508, 1658, 2929, 3062, 3178, (4-bromophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one (5f) Yield: 85%, (0.269 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 1.69 (s, 3H), 5.82 (s, 1H), 6.68 (d, 1H, J=8.1 Hz ), 6.92 (t, 1H, J=7.7 Hz), (m, 1H), 7.43 (d, 2H, J=8.4 Hz), 7.55 (d, 2H, J=8.4 Hz), 7.94 (d, 1H, J=7.8 Hz) ; 13 C NMR (75 MHz, CDCl 3 ): δ 27.9, 84.8,, 114.9, 117.9, 127.6, 127.8, 128.8, 130.3, 130.9, 132.4, 133.9, 141.1, 147.7, 163.9; IR (KBr) cm -1 : 1614, 1488, 1510, 1655, 2931, 3066, 3180, methyl-2-(4-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one (5g) 16
17 Yield: 89%, (0.252 g); M.p C; Characteristics: Yellow crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 1.72 (s, 3H), 5.88 (s, 1H), 6.67 (d, 1H, J=8.1 Hz ), 6.90 (t, 1H, J=7.5 Hz), (m, 5H), 7.95 (d, 1H, J=7.8 Hz); 13 C NMR (75 MHz, DMSO-d 6 ): δ 25.7, 82.7,, 114.9, 117.9, 127.6, 127.8, 128.8, 130.3, 130.9, 132.4, 133.9, 141.1, 147.7, 163.8; IR (KBr) cm -1 : 1615, 1479, 1508, 1658, 2926, 3066, 3182, (4-fluorophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one (5h) Yield: 87%, (0.223 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, CDCl 3 ): δ 1.72 (s, 3H), 6.39 (s, 1H), 6.60 (d, 1H, J=7.8 Hz ), 6.76 (t, 1H, J=7.5 Hz ), 6.94 (t, 2H, J=8.6 Hz ), 7.07 (s, 1H), 7.23 (t, 2H, J=8.1 Hz ), (m, 2H), 7.93; 13 C NMR (75 MHz, CDCl 3 ): δ 28.8, 70.6,, 114.9, 117.9, 127.6, 127.8, 128.8, 130.3, 130.9, 132.4, 133.9, 141.1, 147.7, ; IR (KBr) cm -1 : 1610, 1482, 1508, 1658, 2929, 3066, 3183, 'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one (5i) 17
18 Yield: 95%, (0.205 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ (m, 10H), 6.64 (s, 1H), 6.82 (d, 1H, J=8.1 Hz ), 7.23 (m, 2H), 7.57 (d, 1H, J=7.5 Hz ), 7.94 (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 21.3, 25.1, 68.2, 114.9, 116.9, 127.5, 133.5, 147.2, ; IR (KBr) cm -1 : 1618, 1658, 2927, 3183, 'H-spiro[cyclopentane-1,2'-quinazolin]-4'(3'H)-one (5j) Yield: 95%, (0.192 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): (m, 8H), (m, 2H), (m, 1H), 7.75 (d, 1H, J=7.8 Hz), 7.94 (s, 1H), 8.09 (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 22.4, 29.4, 67.2, 77.5, 115.0, 116.8, 127.6, 133.4, 147.9, 163.8; IR (KBr) cm -1 : 1616, 1655, 2933, 3178, (2-methoxyphenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one (5k) Yield: 87%, ( g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): 1.69 (s, 3H), 3.87 (s, 3H), 5.69 (s, 1H), (m, 3H),
19 (m, 2H), 7.35 (d, 2H, J=7.8 Hz), 7.59 (d, 1H, J=7.5 Hz), 8.20 (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 28.9, 56.9, 73.1, 114.9, 116.5, 121.6, 123.5, 131.7, 140.4, 147.8, 161.5, ; IR (KBr) cm -1 : 1618, 1657, 2933, 3175, (2,4-dichlorophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one (5l) Yield: 89%, (0.269 g); M.p C; Characteristics: White crystalline solid; 1 H NMR (300 MHz, DMSO-D 6 ): 1.67 (s, 3H), 5.88 (s, 1H), 7.20 (d, 2H, J=7.2 Hz), 7.44 (d, 1H, J=7.5 Hz), (m, 2H), 7.87 (dd, 2H, J=7.9 Hz, J=1.4 Hz), 9.69 (s, 1H) ; 13 C NMR (75 MHz, DMSO- D 6 ): δ 21.1, 66.8, 114.8, 115.4, 117.5, 127.1, 127.8, 129.2, 133.7, 138.1, 139.1, 148.2, 164.1; IR (KBr) cm -1 : 1615, 1659, 2930, 31878, (4-nitrophenyl)quinazolin-4(3H)-one (6a) Yield: 97%, (0.259 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, CDCl 3 ): δ 7.53 (d, 1H, J=6.6 Hz), (m, 4H), (m, 3H), (s, 1H); 13 C NMR (75 MHz, DMSO-D 6 ): δ 114.8, 114.9, 117.8, 127.7, 127.8, 129.0, 129.9, 130.6, 132.1, 133.7, 138.2, 147.9, 163.9; HRMS (ESI-TOF) m/z Calculated for [C 14 H 9 N 3 O 3 +Na] + : , found: 19
20 ; IR (KBr) cm -1 : 1663, phenylquinazolin-4(3H)-one (6b) Yield: 94%, (0.208 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, CDCl 3 ): δ 7.52 (t, 2H, J= 7.1 Hz), (m, 5H), (m, 2H), (s, 1H); 13 C NMR (75 MHz, DMSO-D 6 ): δ 117.7, 127.8, 128.8, 129.2, 133.4, 133.9, 141.1, 148.1, 152.0, 158.1, 163.9; IR (KBr) cm -1 : 1661, (3-nitrophenyl)quinazolin-4(3H)-one (6c) Yield: 96%, (0.256 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ (m, 2H), 7.22 (t,1h, J=7.7 Hz ), (m, 2H), (m, 1H), 7.61 (dd, 2H, J=6.0 Hz, J=2.7 Hz) ; 13 C NMR (75 MHz, DMSO-D 6 ): 114.8, 114.9, 117.8, 127.7, 127.8, 129.1, 129.8, 130.6, 132.1, 133.7, 138.2, 147.9, 163.9; IR (KBr) cm -1 : 1659,
21 2-(2-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one (6d) Yield: 95%, (0.243 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, DMSO-D 6 ): (m, 2H), 7.25 (t, 1H, J= 7.7 Hz), (m, 2H), (m,1h), 7.65 (d, 2H, J=6.6 Hz) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 117.9, 127.8, 127.9, 129.2, 130.1, 130.7, 133.9, 148.1, 157.1, 164.1; HRMS (ESI-TOF) m/z Calculated for [C 14 H 9 ClN 2 O+K] + : , found: IR (KBr) cm -1 : 1653, (thiophen-2-yl)-2,3-dihydroquinazolin-4(1H)-one (6e) Yield:90%, (0.205 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ (m, 2H), (m, 1H), (m, 1H), (m, 1H), 7.40 (d, 1H, J=5.1), 7.57 (d, 1H, J=7.5); 13 C NMR (75 MHz, DMSO-D 6 ): δ 117.6, 125.7, 125.9, 126.6, 127.4, 133.5, 146.6, 147.2, 163.2; HRMS (ESI-TOF) m/z Calculated for [C 12 H 9 N 2 OS+K] + : , found: ; IR (KBr) cm -1 : 1637, isopropylquinazolin-4(3H)-one (6f) 21
22 Yield: 88%, (0.165 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ 0.83 (d, 6H, J=6.6Hz), (m, 1H), 6.53 (t, 1H, J=7.4Hz), 6.67 (d, 1H, J=8.1Hz), 7.12 (t, 1H, J=7.5Hz), 7.48 (d, 1H, J=7.5Hz), 9.07 (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 30.7, 32.8, 114.2, 114.8, 116.6, 127.3, 133.1, 148.6, IR (KBr) cm -1 : 1250, 1369, 1457, 1651, (furan-2-yl)quinazolin-4(3H)-one (6g) Yield: 90%, (0.190 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ (m, 2H), (m, 1H), (m, 1H), (m, 1H), 7.40 (d, 1H, J=5.1), 7.57 (d, 1H, J=7.5); 13 C NMR (75 MHz, DMSO-D 6 ): δ 117.6, 125.7, 125.9, 126.6, 127.4, 133.5, 146.6, 147.2, 163.2; IR (KBr) cm -1 : 1370, 1457, 1652, (1H-indol-3-yl)quinazolin-4(3H)-one (6h) Yield: 95%, (0.247 g); M.p C; Characteristics: Yellow solid; 22
23 1 H NMR (300 MHz, DMSO-D 6 ): δ (m, 4H), (m, 5H), 9.75 (s, 1H), (s, 1H); 13 C NMR (75 MHz, DMSO-D 6 ): δ 111.8, 118.3, 118.7, 119.6, 121.0, 123.6, 127.2, 136.9, 149.6, 162.9; IR (KBr) cm -1 : 1376, 1457, 1651, (quinolin-2-yl)quinazolin-4(3H)-one (6i) Yield: 95%, (0.259 g); M.p C; Characteristics: White solid; 1 H NMR (300 MHz, DMSO-D 6 ): δ (m, 5H), 8.12 (d, 1H, J=7.5), 8.25 (t, 2H, J=7.6), (m, 2H), (s, 1H); 13 C NMR (75 MHz, DMSO-D 6 ): δ 115.2, 119.6, 122.5, 122.6, 124.1, 127.5, 130.6, 140.2, 145.2, 152.5, 168.1; IR (KBr) cm -1 : 1675, (2,2-dimethyl-4-oxopentyl)quinazolin-4(3H)-one (7a) Yield: 69%, (0.178 g); M.p C; Characteristics: White solid 1 H NMR (300 MHz, DMSO-D 6 ): δ 1.00 (s, 6H), 2.31 (s, 2H), 2.52 (s, 2H), 2.71 (s, 3H), 7.50 (t, 1H, J=7.1), 7.58 (d, 1H, J=7.8), 7.77 (d, 1H, J=7.5), 8.08 (d, 1H, J=7.8), (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 26.2, 30.1, 33.2, 43.9, 53.6, 121.1, 127.1, 133.5, 142.6, 148.9, 153.9, 164.2; IR (KBr) cm -1 : 1659, (4-oxopentyl)quinazolin-4(3H)-one (7b) 23
24 Yield: 85%, (0.195 g); M.p C; Characteristics: White solid 1 H NMR (300 MHz, DMSO-D 6 ): δ 1.49 (t, 2H, J=5.1), 1.65 (m, 2H), 1.98 (s, 3H), 2.63 (t, 2H, J=5.1) (m, 1H), 7.69 (d, 1H, J=7.8), 7.79 (t, 1H, J=7.7), 8.29 (d, 1H, J=7.8), (s, 1H) ; 13 C NMR (75 MHz, DMSO-D 6 ): δ 22.1, 30.1, 33.2, 43.4, 120.6, 127.1, 133.4, 142.6, 148.9, 153.9, 164.3; IR (KBr) cm -1 : 1659, methylquinazolin-4(3H)-one (8a)/ (8b)/ (8c) Yield: 98%, (0.156 g); M.p C; Characteristics: White solid 1 H NMR (300 MHz, CDCl 3 ): δ 2.61 (s, 3H), (m, 1H), 7.69 (d, 1H, J=7.8), 7.78 (t, 1H, J=7.7), 8.29 (d, 1H, J=7.8), (s, 1H); 13 C NMR (75 MHz, DMSO-D 6 ): δ 22.4, 120.5, 127.6, 133.4, 138.5, 147.9, 154.9, 163.8; IR (KBr) cm -1 : 1665,
25 1 HNMR, 13 CNMR Spectra of the Compounds (3a-3i): 1 H NMR of Compound 3a 13 C NMR of Compound 3a 25
26 1 H NMR of Compound 3b 13 C NMR of Compound 3b 26
27 1 H NMR of Compound 3c 13 C NMR of Compound 3c 27
28 1 H NMR of Compound 3d 13 C NMR of Compound 3d 28
29 1 H NMR of Compound 3e 13 C NMR of Compound 3e 29
30 1 H NMR of Compound 3f 13 C NMR of Compound 3f 30
31 1 H NMR of Compound 3g 13 C NMR of Compound 3g 31
32 1 H NMR of Compound 3h 13 C NMR of Compound 3h 32
33 1 H NMR of Compound 3i 13 C NMR of Compound 3i 33
34 1 H NMR of Compound 3j 13 C NMR of Compound 3j 34
35 1 H NMR of Compound 3k 13 C NMR of Compound 3k 35
36 1 H NMR of Compound 3l 13 C NMR of Compound 3l 36
37 1 H NMR of Compound 3m 13 C NMR of Compound 3m 37
38 1 H NMR of Compound 3n 13 C NMR of Compound 3n 38
39 1 H NMR of Compound 3o 13 C NMR of Compound 3o 39
40 1 H NMR of Compound 3p 13 C NMR of Compound 3p 40
41 1 H NMR of Compound 3q 13 C NMR of Compound 3q 41
42 1 H NMR of Compound 3r 13 C NMR of Compound 3r 42
43 1 H NMR of Compound 3r 13 C NMR of Compound 3s 43
44 1 HNMR, 13 CNMR Spectra of the Compounds (5a-5l)): 1 H NMR of Compound 5a 13 C NMR of Compound 5a 44
45 1 H NMR of Compound 5b 13 C NMR of Compound 5b 45
46 1 H NMR of Compound 5c 13 C NMR of Compound 5c 46
47 1 H NMR of Compound 5d 13 C NMR of Compound 5d 47
48 1 H NMR of Compound 5e 13 C NMR of Compound 5e 48
49 1 H NMR of Compound 5f 13 C NMR of Compound 5f 49
50 1 H NMR of Compound 5g 13 C NMR ofcompound 5g 50
51 1 H NMR of Compound 5h 13 H CMR of Compound 5h 51
52 1 H NMR of Compound 5i 13 C NMR of Compound 5i 52
53 1 H NMR of Compound 5j 13 C NMR of Compound 5j 53
54 1 H NMR of Compound 5k 13 C NMR of Compound 5k 54
55 1 H NMR of Compound 5l 13 C NMR of Compound 5l 55
56 1 HNMR, 13 CNMR Spectra of the Compounds (6a-6i)): 1 H NMR of Compound 6a 13 C NMR of Compound 6a 56
57 1 H NMR of Compound 6b 13 C NMR of Compound 6b 57
58 1 H NMR of Compound 6c 13 C NMR of Compound 6c 58
59 1 H NMR of Compound 6d 13 C NMR of Compound 6d 59
60 1 H NMR of Compound 6e 13 C NMR of Compound 6e 60
61 1 H NMR of Compound 6f 13 C NMR of Compound 6f 61
62 1 H NMR of Compound 6g 13 C NMR of Compound 6g 62
63 1 H NMR of Compound 6h 13 C NMR of Compound 6h 63
64 1 H NMR of Compound 6i 13 C NMR of Compound 6i 64
65 1 H NMR of Compound 7a 13 C NMR of Compound 7a 65
66 1 H NMR of Compound 7b 13 C NMR of Compound 7b 66
67 1 H NMR of Compound 8a/8b/8c 13 C NMR of Compound 8a/8b/8c 67
68 HRMS of Compound 3c HRMS of Compound 6a 68
69 HRMS of Compound 6d HRMS of Compound 6e 69
70 HRMS of compound 8a 70
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