General Remarks
Solvents, reagents, and chemicals were obtained from Merck (Germany) and Fluka (Switzerland) Chemical Companies. Melting points were taken on a Kofler hot stage apparatus and are uncorrected. The IR spectra were obtained on a Nicolet Magna FT-IR 550 spectrophotometer (potassium bromide disks). Nuclear magnetic resonance spectra were recorded on Bruker FT- 500 spectrometers using tetramethyl silane (TMS) as the internal standard in pure deuterated solvents. Chemical shifts are given in the δ scale in parts per million (ppm) and singlet (s), doublet (d), triplet (t), multiplet (m), and doublets of doublet (dd) are recorded. Mass spectra were recorded on an Agilent Technology (HP) mass spectrometer operating at an ionization potential of 70 eV. The elemental analysis was performed with an Elemetar Analysen system GmbH VarioEL CHNS mode. Purification of all products was conducted by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent. Thin layer chromatography was carried out on silica gel 254 analytical sheets obtained from Fluka. Column chromatography was carried out on the column of silica gel 60 Merck (230–240 mesh) in glass columns (2 or 3 cm diameter) using 15–30 grams of silica gel per one gram of the crude mixture. Transition electron microscope images were recorded on a HITACHI S-4160.
Synthesis Of Silica Encapsulated Spion
For the preparation of SPION, two micro-emulsions were prepared. The first one contained a solution of FeCl3.6H2O (202 mg), FeCl2.4H2O (75 mg), and cetyltrimethylammonium bromide (CTAB) (1.8 g) in 2.045 mL of deionized water as the aqueous phase, and toluene (29 mL) as the organic phase. The second micro-emulsion contained 1.8 g of CTAB in 29 ml toluene and 25% ammonium hydroxide solution (2.65 mL). The two micro-emulsions were mixed in a three-necked flask under vigorous stirring at 7000 rpm at 50°C under a constant flow of N2 gas for 60 min. The dark precipitates were separated using an external magnet and washed with boiling EtOH from impurities. The obtained SPIONs were dried under vacuum for 12 h at room temperature.
For coating magnetic nanoparticles with silica, a solution of 200 µl of tetraethyl orthosilicate (TEOS) in 40 ml ethanol was added to a mixture containing 1 mg of SPION in 10 ml of deionized water under vigorous mechanical stirring followed by the addition of 1.25 ml of aqueous ammonia (25% w/w). After 1 h, the obtained magnetic nanoparticles suspension was magnetically separated and washed twice with deionized water. The SiO2@SPION product was separated and dried under reduced pressure at room temperature for 12 h.
Synthesis Of 2-(Pyridin-2-yl)-1,3,4-oxadiazoleis Ligand
Picolinic acid (10 mmol, 1.231 g) was weighed and added to methanol (15 mL). Then, sulfuric acid (100 µL) was added to the solution and stirred at room temperature for 12h. the reaction mixture was neutralized by the addition of a 0.1 M solution of NaOH. The solvent was evaporated and the product was recrystallized from ethanol. In the next step, methyl picolinate product (5 mmol, 0.685 g) was dissolved in ethanol, and hydrazine (7 mmol, 0.2240 mg) was added. The reaction was stirred at room temperature overnight and the product was purified after the removal of the catalyst by recrystallization from ethyl acetate to form pure 2-((hydrazinyloxy)carbonyl)pyridine. In the next step, 2-((hydrazinyloxy)carbonyl)pyridine (4 mmol, 0.612 g) and KOH (5 mmol, 0.280 g) dissolved in ethanol (15 mL) and then CS2 (4 mmol, 0.304 g) was added. The reaction mixture was stirred under reflux conditions for 18h. After the reaction was completed, 5-(pyridin-2-yl)-1,3,4-oxadiazole-2-thiol ligand was purified by recrystallization from ethanol.
Synthesis Of Cu@py-oxa@spion Catalyst
Silica encapsulated SPION (500 mg) was added to dry ethanol (10 mL) and sonicated for 30 min. after that, 3-(chloropropyl)-trimethoxysilane (10 mmol, 1.987 g) was added and stirred at 70°C for 12h. after that, the product was separated from the reaction mixture by a magnet and washed 3 times by toluene, ethanol, and acetone, respectively. The product was added to dry toluene (10 mL) and sonicated for 30 min. Then, 5-(pyridin-2-yl)-1,3,4-oxadiazole-2-thiol ligand (3 mmol, 0.540 g) was added and stirred for 24h at room temperature. After that, Cu@Py-Oxa@SPION catalyst was separated and washed with toluene, ethanol, and acetone and dried in a vacuum oven for 24h.
Synthesis of 3-alkyl-2-(((4-(2-oxopropyl)-1 H -1,2,3-triazol-1-yl)alkyl)thio)-2,3-dihydroquinazolin-4(1 H )-one derivatives
In the first step, isatoic anhydride (10 mmol, 1.630 g) was added to water, and amine (12.5 mmol) was added. The reaction mixture was stirred at room temperature and the reaction performance was monitored by TLC. After the completion of the reaction, the product was filtered and washed with cold water, and dried in air. To the product (5 mmol) in ethanol (10 mL), was added CS2 (5 mmol, 0.380 g) and stirred under reflux conditions. After the reaction was completed, it was poured onto ice water and the product was filtered and purified by recrystallization from ethyl acetate. To this 3-alkyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one product (5 mmol) in DMF (20 mL), was added K2CO3 (8 mmol, 1.104 g) and propargyl bromide (5 mmol, 0,585 g) and stirred at 75°C for 12h. After the reaction was completed, the 3-alkyl-2-(prop-2-yn-1-ylthio)quinazolin-4(3H)-one product was separated by the addition of the reaction mixture to the ice water mixture, followed by washing in cold water 3 times.
For the synthesis of the products, 3-alkyl-2-(prop-2-yn-1-ylthio)quinazolin-4(3H)-one (3 mmol) was added to ethanol (10 mL), and 2-chloro-N-alkylacetamide (3 mmol), sodium azide (3 mmol), and Cu@Py-Oxa@SPION catalyst (50 mg) as added. The reaction mixture was stirred at room temperature and after the reaction was completed, the catalyst was isolated from the reaction mixture by a magnet. The solvent was removed and the product was purified by recrystallization from ethanol.
Spectral Data Of The Products
N -(2,4-dimethylphenyl)-2-(4-(((3-isopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 9.72 (s, 1H), 8.15 (s, 1H), 8.03 (d, J = 7.9 Hz, 1H), 7.76 (t, J = 7.5 Hz, 1H), 7.60 (d, J = 8.1 Hz, 1H), 7.42 (t, J = 7.5 Hz, 1H), 7.04 (d, J = 3.8 Hz, 3H), 5.31 (s, 2H), 4.59 (s, 3H), 2.09 (s, 6H), 1.53 (d, J = 6.6 Hz, 6H); 13C NMR (126 MHz, DMSO-d6) δ 164.42, 161.07, 156.70, 146.67, 135.46, 134.99, 134.26, 128.17, 127.58, 127.21, 127.18, 126.56, 126.38, 126.23, 123.25, 119.92, 52.82, 46.07, 27.62, 19.56, 18.43. Anal. calcd. For C24H26N6O2S: C, 62.32; H, 5.67; N, 18.17; S, 6.93. Found: C, 62.65; H, 5.39; N, 18.03; S, 7.14; MS (70 eV): m/z = 462 (M+).
N -(3-chlorophenyl)-2-(4-(((3-isopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 9.72 (s, 1H), 8.15 (s, 1H), 8.03 (d, J = 7.9 Hz, 1H), 7.76 (t, J = 7.5 Hz, 1H), 7.60 (d, J = 8.1 Hz, 1H), 7.42 (t, J = 7.5 Hz, 1H), 7.04 (d, J = 3.8 Hz, 3H), 5.31 (s, 2H), 4.59 (s, 3H), 2.09 (s, 6H), 1.53 (d, J = 6.6 Hz, 6H); 13C NMR (126 MHz, DMSO-d6) δ 164.98, 161.41, 156.12, 146.67, 140.22, 134.92, 133.62, 131.06, 127.16, 126.60, 126.53, 126.35, 126.28, 123.93, 120.40, 119.13, 118.03, 52.78, 45.81, 27.46, 19.56. Anal. calcd. For C22H21ClN6O2S: C, 65.35; H, 4.51; N, 17.92; S, 6.84. Found: C, 65.17; H, 4.72; N, 18.08; S, 6.99; MS (70 eV): m/z = 468 (M+).
N -(4-bromophenyl)-2-(4-(((3-isopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 10.61 (s, 1H), 8.22 (s, 1H), 8.05 (d, J = 7.8 Hz, 1H), 7.76 (t, J = 7.6 Hz, 1H), 7.62 (d, J = 8.1 Hz, 1H), 7.58–7.46 (m, 4H), 7.43 (t, J = 7.5 Hz, 1H), 5.33 (s, 2H), 4.62 (s, 3H), 1.56 (d, J = 6.5 Hz, 6H); 13C NMR (126 MHz, DMSO-d6) δ 164.82, 161.44, 156.20, 146.70, 138.22, 134.93, 132.18, 126.56, 126.53, 126.37, 126.34, 126.28, 121.56, 120.42, 115.86, 52.75, 46.09, 27.50, 19.59. Anal. calcd. For C22H21BrN6O2S: C, 51.47; H, 4.12; N, 16.37; S, 6.24. Found: C, 51.74; H, 3.97; N, 16.19; S, 6.07; MS (70 eV): m/z = 512 (M+).
2-(4-(((3-isopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -(4-methylbenzyl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 8.75 (t, J = 5.9 Hz, 1H), 8.12 (s, 1H), 8.04 (dd, J = 8.0, 1.5 Hz, 1H), 7.76 (td, J = 7.7, 7.1, 1.6 Hz, 1H), 7.60 (d, J = 8.1 Hz, 1H), 7.42 (t, J = 7.6 Hz, 1H), 7.11 (q, J = 8.1 Hz, 3H), 5.12 (s, 2H), 4.58 (s, 3H), 4.24 (d, J = 5.8 Hz, 2H), 2.25 (s, 3H), 1.54 (d, J = 6.6 Hz, 6H); 13C NMR (126 MHz, DMSO-d6) δ 165.73, 161.42, 156.24, 146.69, 136.51, 136.07, 134.96, 129.30, 127.81, 126.56, 126.34, 126.24, 126.07, 126.04, 120.42, 52.09, 47.67, 42.55, 27.47, 21.10, 19.56. Anal. calcd. For C24H26N6O2S: C, 62.32; H, 5.67; N, 18.17; S, 6.93. Found: C, 62.16; H, 5.89; N, 18.35; S, 7.16; MS (70 eV): m/z = 462 (M+).
2-(4-(((3-isopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -(4-nitrophenyl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 11.08 (s, 1H), 8.24 (d, J = 9.1 Hz, 2H), 8.21 (s, 1H), 8.05 (dd, J = 8.0, 1.5 Hz, 1H), 7.83–7.75 (m, 3H), 7.63 (d, J = 8.0 Hz, 1H), 7.48–7.40 (m, 1H), 5.40 (s, 2H), 4.62 (s, 3H), 1.56 (d, J = 6.6 Hz, 6H); 13C NMR (126 MHz, DMSO-d6) δ 165.81, 161.45, 156.23, 146.70, 144.95, 143.00, 135.01, 131.63, 128.25, 126.57, 126.55, 126.40, 126.31, 125.60, 119.44, 52.78, 48.62, 27.44, 19.59. Anal. calcd. For C22H21N7O4S: C, 55.11; H, 4.41; N, 20.45; S, 6.69. Found: C, 54.95; H, 4.24; N, 20.29; S, 6.88; MS (70 eV): m/z = 479 (M+).
2-(4-(((3-isopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -phenylacetamide
1H NMR (500 MHz, DMSO-d6) δ 10.43 (s, 1H), 8.19 (s, 1H), 8.03 (d, J = 7.9 Hz, 1H), 7.76 (t, J = 7.7 Hz, 1H), 7.61 (d, J = 7.7 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.42 (t, J = 7.5 Hz, 1H), 7.30 (t, J = 7.7 Hz, 2H), 7.05 (dd, J = 11.6, 5.4 Hz, 2H), 5.29 (s, 2H), 4.60 (s, 3H), 1.54 (d, J = 6.5 Hz, 6H); 13C NMR (126 MHz, DMSO-d6) δ 164.57, 161.43, 156.22, 146.69, 138.82, 135.47, 134.96, 129.34, 128.17, 127.18, 126.55, 126.36, 126.27, 124.19, 119.61, 52.70, 48.79, 27.49, 19.58. Anal. calcd. For C22H22N6O2S: C, 60.81; H, 5.10; N, 19.34; S, 7.38. Found: C, 60.98; H, 5.22; N, 19.56; S, 7.47; MS (70 eV): m/z = 434 (M+).
N -(3,5-dimethylphenyl)-2-(4-(((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 9.72 (s, 1H), 8.13 (s, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.84 (t, J = 7.9 Hz, 1H), 7.71 (d, J = 8.2 Hz, 1H), 7.59–7.36 (m, 7H), 7.05 (s, 3H), 5.31 (s, 2H), 4.48 (s, 2H), 2.11 (s, 6H); 13C NMR (126 MHz, DMSO-d6) δ 164.42, 161.16, 157.12, 147.67, 136.16, 135.49, 135.37, 134.60, 132.17, 130.39, 129.95, 129.85, 128.18, 127.19, 127.02, 126.67, 126.51, 126.02, 120.05, 52.12, 27.28, 18.45. Anal. calcd. For C27H24N6O2S: C, 65.30; H, 4.87; N, 16.92; S, 4.46. Found: C, 65.12; H, 4.69; N, 17.11; S, 4.25; MS (70 eV): m/z = 496 (M+).
N -(3-chlorophenyl)-2-(4-(((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 10.67 (s, 1H), 8.18 (s, 1H), 8.10 (d, J = 7.9 Hz, 1H), 7.79–7.70 (m, 2H), 7.61–7.39 (m, 9H), 7.15 (d, J = 8.3 Hz, 1H), 5.31 (s, 2H), 4.50 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 165.09, 161.19, 157.12, 147.69, 140.26, 136.19, 135.38, 134.61, 133.65, 131.11, 130.43, 129.99, 129.88, 129.74, 127.02, 126.74, 126.53, 123.97, 120.07, 119.15, 118.06, 52.67, 27.31. Anal. calcd. For C25H19ClN6O2S: C, 59.70; H, 3.81; N, 16.71; S, 6.37. Found: C, 59.92; H, 4.01; N, 16.53; S, 6.20; MS (70 eV): m/z = 502 (M+).
N -(4-bromophenyl)-2-(4-(((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 10.57 (s, 1H), 8.12 (s, 1H), 8.08 (d, J = 7.8 Hz, 1H), 7.84 (t, J = 7.7 Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), 7.60–7.40 (m, 10H), 5.27 (s, 2H), 4.47 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 164.82, 161.16, 157.11, 147.67, 138.19, 136.16, 135.37, 132.18, 130.40, 129.96, 129.86, 127.01, 126.71, 126.51, 126.10, 125.56, 121.56, 120.05, 115.83, 52.64, 27.27. Anal. calcd. For C25H19BrN6O2S: C, 54.85; H, 3.50; N, 15.35; S, 5.86. Found: C, 55.02; H, 3.74; N, 15.59; S, 6.01; MS (70 eV): m/z = 546 (M+).
N -(4-nitrophenyl)-2-(4-(((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 11.04 (s, 1H), 8.28–8.11 (m, 3H), 8.07 (d, J = 7.8 Hz, 1H), 7.88–7.66 (m, 5H), 7.60–7.38 (m, 6H), 5.36 (s, 2H), 4.48 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 165.73, 161.15, 157.08, 147.66, 144.91, 142.99, 136.16, 135.36, 131.97, 130.40, 129.96, 129.85, 128.73, 127.00, 126.71, 126.50, 125.53, 120.03, 119.43, 52.78, 27.32; Anal. calcd. For C25H19N7O4S: C, 58.47; H, 3.73; N, 19.09; S, 6.24. Found: C, 58.27; H, 3.66; N, 18.88; S, 6.06; MS (70 eV): m/z = 513 (M+).
2-(4-(((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -phenylacetamide
1H NMR (500 MHz, DMSO-d6) δ 10.44 (s, 1H), 8.15 (s, 1H), 8.08 (d, J = 7.8 Hz, 1H), 7.83 (t, J = 7.8 Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), 7.59–7.49 (m, 5H), 7.50–7.40 (m, 3H), 7.30 (t, J = 7.8 Hz, 2H), 7.06 (t, J = 7.4 Hz, 1H), 5.27 (s, 2H), 4.48 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 164.57, 161.17, 157.10, 147.67, 138.82, 136.16, 135.37, 130.40, 129.96, 129.86, 129.35, 127.00, 126.71, 126.50, 124.20, 120.04, 119.60, 52.67, 27.29; Anal. calcd. For C25H20N6O2S: C, 64.09; H, 4.30; N, 17.94; S, 6.84. Found: C, 63.90; H, 4.51; N, 17.81; S, 7.03; MS (70 eV): m/z = 468 (M+).
2-(4-(((3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -(2,4-dimethylphenyl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 9.72 (s, 1H), 8.12 (s, 1H), 7.82 (t, J = 7.7 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.48 (t, J = 7.5 Hz, 1H), 7.34–7.18 (m, 6H), 7.04 (q, J = 5.0 Hz, 3H), 5.31 (s, 2H), 5.29 (s, 2H), 4.59 (s, 2H), 2.09 (s, 6H); 13C NMR (126 MHz, DMSO-d6) δ 164.39, 161.37, 156.70, 147.26, 136.00, 135.47, 135.39, 134.59, 130.28, 129.04, 128.17, 127.85, 127.18, 127.13, 127.06, 126.63, 126.11, 119.43, 119.20, 52.13, 47.22, 27.06, 18.43. Anal. calcd. For C28H26N6O2S: C, 65.86; H, 5.13; N, 16.46; S, 6.28. Found: C, 65.63; H, 5.00; N, 16.31; S, 6.12; MS (70 eV): m/z = 510 (M+).
2-(4-(((3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -(4-bromophenyl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 10.56 (s, 1H), 8.14–8.09 (m, 2H), 7.83 (t, J = 7.3 Hz, 1H), 7.69 (d, J = 7.7 Hz, 1H), 7.55–7.45 (m, 5H), 7.30 (t, J = 8.0 Hz, 2H), 7.23 (dd, J = 14.0, 7.4 Hz, 3H), 5.30 (s, 2H), 5.27 (s, 2H), 4.59 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 164.82, 161.38, 156.69, 147.27, 136.01, 135.40, 134.81, 133.70, 132.18, 130.15, 129.05, 127.86, 127.13, 127.05, 126.69, 126.66, 126.11, 121.55, 119.20, 52.64, 47.23, 27.00. Anal. calcd. For C26H21BrN6O2S: C, 55.62; H, 3.77; N, 14.97; S, 5.71. Found: C, 55.85; H, 3.47; N, 15.18; S, 5.56; MS (70 eV): m/z = 560 (M+).
2-(4-(((3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -(4-nitrophenyl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 11.08 (s, 1H), 8.23 (d, J = 9.0 Hz, 2H), 8.17 (s, 1H), 8.12 (d, J = 7.9 Hz, 1H), 7.81 (dd, J = 11.4, 8.2 Hz, 3H), 7.69 (d, J = 8.2 Hz, 1H), 7.49 (t, J = 7.6 Hz, 1H), 7.28 (dt, J = 35.0, 7.5 Hz, 5H), 5.39 (s, 2H), 5.31 (s, 2H), 4.62 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 165.77, 161.38, 156.67, 147.27, 144.94, 143.00, 136.02, 135.37, 131.23, 129.06, 128.82, 127.87, 127.16, 127.05, 126.68, 126.63, 125.54, 119.43, 119.20, 52.78, 47.25, 27.06. Anal. calcd. For C26H21N7O4S: C, 59.19; H, 4.01; N, 18.59; S, 6.08. Found: C, 59.33; H, 3.89; N, 18.77; S, 5.91; MS (70 eV): m/z = 527 (M+).
2-(4-(((3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -phenylacetamide
1H NMR (500 MHz, DMSO-d6) δ 10.45 (s, 1H), 8.16 (s, 1H), 8.11 (d, J = 7.9 Hz, 1H), 7.80 (t, J = 7.7 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.56 (d, J = 8.0 Hz, 2H), 7.46 (t, J = 7.6 Hz, 1H), 7.26 (dd, J = 31.9, 8.1 Hz, 8H), 7.06 (t, J = 7.4 Hz, 1H), 5.30 (s, 4H), 4.61 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 164.57, 161.37, 156.66, 147.26, 138.84, 136.01, 135.33, 129.33, 129.03, 128.81, 127.85, 127.17, 127.04, 126.66, 126.59, 126.23, 124.19, 119.63, 119.21, 52.71, 47.24, 27.10. Anal. calcd. For C26H22N6O2S: C, 64.71; H, 4.60; N, 17.42; S, 6.64. Found: C, 46.56; H, 4.82; N, 17.26; S, 6.86; MS (70 eV): m/z = 482 (M+).
2-(4-(((3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)methyl)-1 H -1,2,3-triazol-1-yl)- N -(3-chlorophenyl)acetamide
1H NMR (500 MHz, DMSO-d6) δ 10.66 (s, 1H), 8.20 (s, 1H), 8.12 (d, J = 7.8 Hz, 1H), 7.82 (t, J = 7.4 Hz, 1H), 7.76 (s, 1H), 7.69 (d, J = 8.1 Hz, 1H), 7.48 (t, J = 7.5 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.33 (dt, J = 18.5, 7.6 Hz, 4H), 7.24 (d, J = 7.6 Hz, 3H), 7.14 (d, J = 7.9 Hz, 1H), 5.32 (d, J = 13.3 Hz, 4H), 4.62 (s, 2H); 13C NMR (126 MHz, DMSO-d6) δ 165.01, 161.38, 156.60, 147.26, 140.24, 136.01, 135.34, 133.65, 131.07, 129.05, 127.86, 127.18, 127.05, 126.69, 126.63, 123.95, 119.22, 119.15, 118.04, 52.76, 47.25, 27.06. Anal. calcd. For C26H21ClN6O2S: C, 60.40; H, 4.09; N, 16.26; S, 6.20. Found: C, 60.23; H, 3.85; N, 16.05; S, 5.96; MS (70 eV): m/z = 516 (M+).