Melting points were determined in open capillaries on a Mel-Temp apparatus and are uncorrected. The purity of the compounds was evaluated by TLC (silica gel H, BDH, ethyl acetate/hexane, 1:3). The IR spectra were recorded on a Thermo Nicolet IR 200 FT-IR spectrometer as KBr pellets and the wave numbers were given in cm− 1. The 1H and 13C NMR spectra were recorded in DMSO-d6 on a Bruker spectrometer operating at 400 and 100 MHz. The chemical shifts are reported in δ (ppm) using TMS as an internal standard. The high-resolution mass spectra are recorded on micromass Q-TOF micromass spectrometer using electrospray ionization. Ultrasonication was performed in a Bandelinsonorex RK 12 H ultrasonic bath operating at a frequency of 35 KHz. The microanalyses were performed on a Perkin-Elmer 240C elemental analyzer. The progress of the reaction was monitored by TLC using silica gel plates (silica gel 60 F254 0.25 mm), and components were visualized by observation under UV light (254 and 365 nm). The compounds 4-thiophenyloxazolyl-2-amine (1) and 4-thiophenylthiazolyl-2-amine (2) 4-thiophenylimidazolyl-2-amine (3) were prepared as per the literature procedures [Taterao et al. 2008]. The compound 4-(4-chlorophenyl)-1H-pyrrol-2-amine (7) was purchased from Aldrich.
Preparation of dispersed sodium
Clean sodium metal (10 g) was weighed under dry ether and introduced into a 500 ml round-bottomed flask containing sodium-dried xylene (100 cm3) fitted with an air condenser carrying a calcium chloride guard tube and placed on a sand bath. The flask was enveloped with a dry cloth and the sand bath was heated cautiously. The ring of condensed vapour of xylene was carefully observed. When the ring of condensed vapor had risen to the neck of the flask the flame was extinguished. The condenser was replaced by the stopper and the flask was wrapped with a pre-dried cloth. The stopper was then held firmly and shaken vigorously for 2–3 min until the molten sodium was converted into a fine dispersion. Immediately the stopper was removed and the flask was placed on the cork ring. The sodium was obtained in the form of small spheres depending upon the time and rapidity of shaking. Then the contents were cooled to room temperature, xylene was decanted and the sodium was washed with sodium-dried ether. The dispersed sodium as small spheres was preserved in absolute ether.
General procedure for the synthesis of methyl 4-thiophenylazolylsulfamoyl acetate (4/5/6)
A mixture of methyl 2-chlorosulfonylacetate (0.001 mol), dispersed sodium (0.0414 g, 1.8 mg atom) and tetrahydrofuran (3 ml) was sonicated for 8 min in a sonic bath at a frequency of 35 KHz at 250C. To this azolyl-2-amine (1/2/3) was added and continued sonication for 12–16 min. After completion of the reaction (monitored by TLC), the organic matter was filtered, washed with water, extracted with ether and dried. Removal of the solvent under reduced pressure gave a solid which was recrystallized from ethanol.
Methyl 2-(N-(4-(4-chlorothiophen-2-yl)oxazol-2-yl)sulfamoyl)acetate (4a). Yield 75%; m.p.: 122-124°C; IR (KBr): 1129, 1327 (SO2), 1579 (C = N), 1632 (C = C), 1680 (C = O), 3356 (NH) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 3.68 (s, 3H, O-CH3), 4.36 (s, 2H, CH2), 7.07 (s, 1H, C5'-H), 7.35 (s, 1H, C3'-H), 7.58 (s, 1H, C5-H), 10.46 (bs, 1H, SO2NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 49.1 (O-CH3), 70.4 (CH2), 121.9, 123.7, 125.4, 127.2, 141.5, 145.1, 146.6 (Aromatic carbons C-2, C-4, C-5, C-2', C-3', C-4' & C-5'), 163.0 (C = O) ppm; HRMS (m/z): 359.7513 [M + Na]; Anal. Calcd. for C10H9ClN2O5S2: C, 35.67; H, 2.69; N, 8.32; Found: C, 35.74; H, 2.63; N, 8.41%.
Methyl 2-(N-(4-(4-nitrothiophen-2-yl)oxazol-2-yl)sulfamoyl)acetate (4b). Yield 72%; m.p.: 145-147°C; IR (KBr): 1135, 1321 (SO2), 1587 (C = N), 1650 (C = C), 1676 (C = O), 3367 (NH) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 3.64 (s, 3H, O-CH3), 4.34 (s, 2H, CH2), 7.61 (s, 1H, C5-H), 8.39 (s, 1H, C5'-H), 8.66 (s, 1H, C3'-H), 10.48 (bs, 1H, SO2NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 51.9 (O-CH3), 65.6 (CH2), 117.3, 127.1, 132.6, 138.0, 146.5, 149.4, 153.2 (Aromatic carbons C-2, C-4, C-5, C-2', C-3', C-4' & C-5'), 162.8 (C = O) ppm; HRMS (m/z): 370.3051 [M + Na]; Anal. Calcd. for C10H9N3O7S2 : C, 34.58; H, 2.61; N, 12.10; Found: C, 34.50; H, 2.66; N, 12.26%.
Methyl 2-(N-(4-(4-chlorothiophen-2-yl)thiazol-2-yl)sulfamoyl)acetate (5a). Yield 76%; m.p.: 138-140°C; IR (KBr): 1143, 1335 (SO2), 1583 (C = N), 1643 (C = C), 1688 (C = O), 3365 (NH) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 3.70 (s, 3H, O-CH3), 4.32 (s, 2H, CH2), 7.02 (s, 1H, C5-H), 7.10 (s, 1H, C5'-H), 7.41 (s, 1H, C3'-H), 10.44 (bs, 1H, SO2NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 49.7 (O-CH3), 63.2 (CH2), 105.2 (C-5), 124.3, 127.0, 131.5, 140.3, 145.1 (Aromatic carbons C-4, C-2', C-3', C-4' & C-5'), 162.6 (C = O), 165.4 (C-2) ppm; HRMS (m/z): 375.8122 [M + Na]; Anal. Calcd. for C10H9ClN2O4S3: C, 34.04; H, 2.57; N, 7.94; Found: C, 33.98; H, 2.62; N, 7.99%.
Methyl 2-(N-(4-(4-nitrothiophen-2-yl)thiazol-2-yl)sulfamoyl)acetate (5b). Yield 74%; m.p.: 163-165°C; IR (KBr): 1124, 1341 (SO2), 1578 (C = N), 1652 (C = C), 1674 (C = O), 3371 (NH) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 3.74 (s, 3H, O-CH3), 4.36 (s, 2H, CH2), 7.05 (s, 1H, C5-H), 8.35 (s, 1H, C5'-H), 8.69 (s, 1H, C3'-H), 10.42 (bs, 1H, SO2NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 50.2 (O-CH3), 64.5 (CH2), 106.7 (C-5), 117.2 (C-3'), 128.7, 144.5, 146.4, 152.3 (Aromatic carbons C-4, C-2', C-4' & C-5'), 162.1 (C = O), 169.6 (C-2) ppm; HRMS (m/z): 386.3673 [M + Na]; Anal. Calcd. for C10H9N3O6S3: C, 33.05; H, 2.50; N, 11.56; Found: C, 33.12; H, 2.54; N, 11.65%.
Methyl 2-(N-(4-(4-chlorothiophen-2-yl)-1H-imidazol-2-yl)sulfamoyl)acetate (6a). Yield 77%; m.p.: 149-151°C; IR (KBr): 1148, 1330 (SO2), 1585 (C = N), 1645 (C = C), 1687 (C = O), 3377 (NH) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 3.69 (s, 3H, O-CH3), 4.31 (s, 2H, CH2), 7.06 (s, 1H, C5'-H), 7.37 (s, 1H, C3'-H), 7.40 (s, 1H, C5-H), 10.38 (bs, 1H, SO2NH), 12.88 (bs, 1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 51.8 (O-CH3), 61.0 (CH2), 121.3, 123.1, 125.1, 128.6, 139.4, 143.2, 154.5 (Aromatic carbons C-2, C-4, C-5, C-2', C-3', C-4' & C-5'), 163.7 (C = O) ppm; HRMS (m/z): 358.7672 [M + Na]; Anal. Calcd. for C10H10ClN3O4S2: C, 35.77; H, 3.00; N, 12.51; Found: C, 35.84; H, 3.04; N, 12.44%.
Methyl 2-(N-(4-(4-nitrothiophen-2-yl)-1H-imidazol-2-yl)sulfamoyl)acetate (6b). Yield 75%; m.p.: 178-180°C; IR (KBr): 1136, 1322 (SO2), 1588 (C = N), 1633 (C = C), 1675 (C = O), 3380 (NH) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 3.73 (s, 3H, O-CH3), 4.38 (s, 2H, CH2), 7.42 (s, 1H, C5-H), 8.38 (s, 1H, C5'-H), 8.65 (s, 1H, C3'-H), 10.40 (bs, 1H, SO2NH), 12.90 (bs, 1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 52.3 (O-CH3), 62.1 (CH2), 122.9, 124.8, 133.4, 139.0, 146.8, 152.9, 154.1 (Aromatic carbons C-2, C-4, C-5, C-2', C-3', C-4' & C-5'), 165.4 (C = O) ppm; HRMS (m/z): 369.3224 [M + Na]; Anal. Calcd. for C10H10N4O6S2: C, 34.68; H, 2.91; N, 16.18; Found: C, 34.62; H, 2.62; N, 16.15%
General procedure for the synthesis of N-(4-(4-chlorothiophen-2-yl)oxazol / thiazol / imidazol-2-yl)-2-(N-(4-phenyl-1H-pyrrol-2-yl)sulfamoyl) acetamide (8/9/10)
A mixture of sodium methoxide (0.0011 mol), 4-phenyl-1H-pyrrol-2-amine (7) and methanol (5 ml) was sonicated at a frequency of 35 KHz at room temperature for 5 min. To this thiophenyl azolyl sulfamoyl acetate (4/5/6) (0.001 mol) was added and continued sonication for 22–30 min. The solvent was evaporated under reduced pressure. The gummy substance was recrystallized from ethanol.
N-(4-(4-Chlorothiophen-2-yl)oxazol-2-yl)-2-(N-(4-phenyl-1H-pyrrol-2-yl)sulfamoyl)acetamide (8a) yield 64% ; m.p.: 149-151oC; IR (KBr): 3375 (CONH), 1712 (C = O), 1678 (C = C), 1579 (C = N), 1326 − 1132 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.28 (s, 2H, CH2), 6.60 (s, 1H, C3''-H), 7.05 (s, 1H, C5''-H), 7.14 (s, 1H, C5'-H), 7.40–7.66 (m, 7H, Ar-H, C3'-H & C5-H), 9.92 (bs, 1H, CONH2), 10.32 (bs, 1H, NH), 11.45 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 64.2 (H2C-CO), 104.1 (C-3''), 116.3 (C-5''), 118.8 (C-5'), 144.0 (C-2'), 151.4 (C-2), 169.8 (C = O), 121.3, 122.1, 123.5, 125.9, 126.7, 127.8, 133.3, 136.1, 138.5, 139.7 (Aromatic carbons & C-4, C-5, C-3', C-4', C-2'', C-4'') ppm. HRMS (m/z): 485.9126 [M + Na]+; Anal. Calcd. for C19H15ClN4O4S2: C, 49.30; H, 3.27; N, 12.10; Found: C, 49.39; H, 3.35; N, 12.18%.
N-(4-(4-Nitrothiophen-2-yl)oxazol-2-yl)-2-(N-(4-phenyl-1H-pyrrol-2-yl)sulfamoyl)acetamide (8b) yield 68% ; m.p.: 153-155oC; IR (KBr): 3381 (CONH), 1688 (C = O), 1679 (C = C), 1577 (C = N), 1332 − 1140 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.29 (s, 2H, CH2), 6.58 (s, 1H, C3''-H), 7.08 (s, 1H, C5''-H), 7.42–7.72 (m, 6H, Ar-H & C5-H), 8.42 (s, 1H, C5'-H), 8.79 (s, 1H, C3'-H), 9.95 (bs, 1H, CONH2), 10.49 (bs, 1H, NH), 11.66 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 65.1 (H2C-CO), 106.6 (C-3''), 116.7 (C-5''), 118.5 (C-3'), 124.1 (C-4), 144.3 (C-2'), 149.1 (C-4'), 152.6 (C-2), 170.4 (C = O), 125.8, 128.5, 130.7, 132.4, 134.9, 135.6, 136.8, 137.6 (Aromatic carbons & C-5, C-5', C-2'', C-4'') ppm. HRMS (m/z): 496.4676 [M + Na]+; Anal. Calcd. for C19H15N5O6S2: C, 48.20; H, 3.19; N, 14.79; Found: C, 48.27; H, 3.14; N, 14.68%.
2-(N-(4-(4-Chlorophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-chlorothiophen-2-yl)oxazol-2-yl) acetamide (8c) yield 67% ; m.p.: 159-161oC; IR (KBr): 3377 (CONH), 1722 (C = O), 1680 (C = C), 1582 (C = N), 1335 − 1132 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.27 (s, 2H, CH2), 6.56 (s, 1H, C3''-H), 7.04 (s, 1H, C5''-H), 7.15 (s, 1H, C5'-H), 7.58–7.84 (m, 6H, Ar-H C5-H & C3'-H), 10.26 (bs, 1H, CONH2), 10.41 (bs, 1H, NH), 11.81 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 65.2 (H2C-CO), 106.3 (C-3''), 117.9 (C-5''), 119.2 (C-3'), 121.2 (C-5'), 140.7 (C-5), 145.6 (C-2'), 154.3 (C-2), 170.3 (C = O), 125.1, 126.3, 127.2, 130.5, 132.2, 135.4, 136.5, 137.3 (Aromatic carbons & C-4, C-4', C-2'', C-4'') ppm; HRMS (m/z): 520.3850 [M + Na]+; Anal. Calcd. for C19H14Cl2N4O4S2: C, 45.88; H, 2.84; N, 11.26; Found: C, 45.80; H, 2.80; N, 11.18 %.
2-(N-(4-(4-Chlorophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-nitrothiophen-2-yl)oxazol-2-yl) acetamide (8d) yield 70%; m.p.: 165-167oC; IR (KBr): 3372 (CONH), 1702 (C = O), 1684 (C = C), 1568 (C = N), 1335 − 1128 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.26 (s, 2H, CH2), 6.61 (s, 1H, C3''-H), 7.12 (s, 1H, C5''-H), 7.64–7.83 (m, 5H, Ar-H & C5-H), 8.44 (s, 1H, C5'-H), 8.75 (s, 1H, C3'-H), 10.20 (bs, 1H, CONH2), 10.48 (bs, 1H, NH), 11.93 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 64.5 (H2C-CO), 107.2 (C-3''), 114.5 (C-3'), 117.3 (C-5''), 142.8 (C-2'), 154.1 (C-2), 172.1 (C = O), 149.8 (C-4'), 123.1, 125.2, 127.4, 128.8, 129.5, 132.6, 134.1, 137.9, 139.2 (Aromatic carbons, C-4, C-5, C-5', C-2'' & C-4'') ppm. HRMS (m/z): 530.9095 [M + Na]+; Anal. Calcd. for C19H14ClN5O6S2: C, 44.93; H, 2.78; N, 13.79; Found: C, 45.00; H, 2.74; N, 13.85 %.
N-(4-(4-Chlorothiophen-2-yl)oxazol-2-yl)-2-(N-(4-(4-nitrophenyl)-1H-pyrrol-2-yl)sulfamoyl) acetamide (8e) yield 66%; m.p.: 160-162oC; IR (KBr): 3380 (CONH), 1721 (C = O), 1676 (C = C), 1575 (C = N), 1339 − 1141 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.20 (s, 2H, CH2), 6.74 (s, 1H, C3''-H), 7.13 (s, 1H, C5''-H), 7.19 (s, 1H, C5'-H), 7.59–7.75 (m, 6H, Ar-H, C3'-H & C5-H), 10.15 (bs, 1H, CONH2), 10.65 (bs, 1H, NH), 12.04 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 65.8 (H2C-CO), 107.4 (C-3''), 118.3 (C-5''), 144.3 (C-2'), 152.5 (C-2), 172.5 (C = O), 124.2, 126.8, 128.5, 129.4, 130.5, 132.3, 134.1, 135.8, 137.6, 138.5, 139.3 (Aromatic carbons, C-4, C-5, C-3', C-4', C-5', C-2'' & C-4'') ppm. HRMS (m/z): 530.9103 [M + Na]+; Anal. Calcd. for C19H14ClN5O6S2: C, 44.93; H, 2.78; N, 13.79; Found: C, 44.85; H, 2.83; N, 13.87 %.
2-(N-(4-(4-Nitrophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-nitrothiophen-2-yl)oxazol-2-yl) acetamide (8f) yield 68% ; m.p.: 174-176oC; IR (KBr): 3385 (CONH), 1736 (C = O), 1687 (C = C), 1584 (C = N), 1343 − 1148 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.26 (s, 2H, CH2), 6.70 (s, 1H, C3''-H), 7.14 (s, 1H, C5''-H), 7.60–7.83 (m, 5H, Ar-H & C5-H), 8.32 (s, 1H, C5'-H), 8.65 (s, 1H, C3'-H), 10.61 (bs, 1H, CONH2), 10.72 (bs,1H, NH), 12.09 (bs,1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 66.4 (H2C-CO), 107.8 (C-3''), 117.3 (C-5''), 118.6 (C-3'), 128.4 (C-4), 144.3 (C-2'), 150.6 (C-4'), 153.9 (C-2), 172.6 (C = O), 127.7, 128.3, 129.2, 130.4, 133.7, 135.9, 139.8, 140.6 (C-5, C-5', C-2'', C-4'' & Aromatic carbons) ppm. HRMS (m/z): 541.4654 [M + Na]+; Anal. Calcd. for C19H14N6O8S2: C, 44.02; H, 2.72; N, 16.21; Found: C, 44.10; H, 2.76; N, 16.34 %.
N-(4-(4-Chlorothiophen-2-yl)thiazol-2-yl)-2-(N-(4-phenyl-1H-pyrrol-2-yl)sulfamoyl)acetamide (9a) yield 72% ; m.p.: 135-137oC; IR (KBr): 3373 (CONH), 1689 (C = O), 1670 (C = C), 1568 (C = N), 1335 − 1130 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.31 (s, 2H, CH2), 6.61 (s, 1H, C3''-H), 7.07 (s, 1H, C5''-H), 7.20–7.68 (m, 7H, Ar-H, C3'-H & C5'-H), 7.86 (s, 1H, C5-H), 10.14 (bs, 1H, CONH), 10.46 (bs, 1H, SO2, NH), 11.52 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 64.7 (H2C-CO), 104.2 (C-3''), 105.9 (C-5), 116.5 (C-5''), 119.8 (C-5'), 145.5 (C-2'), 146.3 (C-4), 164.7 (C-2), 170.4 (C = O), 124.3, 125.2, 127.3, 128.9, 130.5, 133.6, 136.4, 139.2 (Aromatic carbons, C-3', C-4', C-2'' & C-4'') ppm. HRMS (m/z): 501.9743 [M + Na]+; Anal. Calcd. for C19H15ClN4O3S3: C, 47.64; H, 3.16; N, 11.70; Found: C, 47.70; H, 3.20; N, 11.78 %.
N-(4-(4-Nitrothiophen-2-yl)thiazol-2-yl)-2-(N-(4-phenyl-1H-pyrrol-2-yl)sulfamoyl)acetamide (9b) yield 65% ; m.p.: 148-150oC; IR (KBr): 3379 (CONH), 1718 (C = O), 1671 (C = C), 1573 (C = N), 1323 − 1134 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.30 (s, 2H, CH2), 6.63 (s, 1H, C3''-H), 7.12 (s, 1H, C5''-H), 7.47–7.73 (m, 5H, Ar-H), 7.80 (s, 1H, C5-H), 8.46 (s, 1H, C5'-H), 8.84 (s, 1H, C3'-H), 10.28 (bs, 1H, CONH2), 10.52 (bs, 1H, NH), 11.59 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 66.2 (H2C-CO), 105.8 (C-3''), 106.5 (C-5), 119.2 (C-3'), 117.6 (C-5''), 144.3 (C-2'), 147.5 (C-4), 149.1 (C-4'), 163.8 (C-2), 171.3 (C = O), 126.5, 128.2, 129.1, 131.4, 135.2, 136.6, 138.1 (Aromatic carbons, C-2'', C-4'' & C-5') ppm. HRMS (m/z): 512.5285 [M + Na]+; Anal. Calcd. for C19H15N5O5S3: C, 46.62; H, 3.09; N, 14.31; Found: C, 46.53; H, 3.05; N, 14.39 %.
2-(N-(4-(4-Chlorophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-chlorothiophen-2-yl)thiazol-2-yl) acetamide (9c) yield 65% ; m.p.: 154-156oC; IR (KBr): 3366 (CONH), 1715 (C = O), 1672 (C = C), 1578 (C = N), 1342 − 1146 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.32 (s, 2H, CH2), 6.62 (s, 1H, C3''-H), 7.01 (s, 1H, C5''-H), 7.17 (s, 1H, C5'-H), 7.44 (s, 1H, C3'-H), 7.62–7.87 (m, 5H, Ar-H & C5-H), 10.41 (bs, 1H, CONH2), 10.63 (bs,1H, NH), 11.78 (bs,1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 66.1 (H2C-CO), 105.9 (C-5), 106.6 (C-3''), 117.1 (C-5''), 145.8 (C-4), 146.1 (C-2'), 163.6 (C-2), 171.1 (C = O), 121.9, 123.5, 125.3, 126.2, 127.6, 131.3, 134.2, 138.6, 139.4 (Aromatic carbons, C-3', C-4', C-5', C-2'' & C-4'') ppm. HRMS (m/z): 536.4152 [M + Na]+; Anal. Calcd. for C19H14Cl2N4O3S3: C, 44.45; H, 2.75; N, 10.91; Found: C, 44.35; H, 2.72; N, 10.80 %.
2-(N-(4-(4-Chlorophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-nitrothiophen-2-yl)thiazol-2-yl) acetamide (9d) yield 68% ; m.p.: 162-164oC; IR (KBr): 3368 (CONH), 1689 (C = O), 1677 (C = C), 1572 (C = N), 1344 − 1136 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.33 (s, 2H, CH2), 6.65 (s, 1H, C3''-H), 7.15 (s, 1H, C5''-H), 7.56–7.85 (m, 5H, Ar-H & C5-H), 8.49 (s, 1H, C5'-H), 8.82 (s, 1H, C3'-H), 10.31 (bs, 1H, CONH2), 10.60 (bs, 1H, NH), 11.98 (bs, 1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 65.6 (H2C-CO), 106.8 (C-5), 107.9 (C-3''), 116.3 (C-5''), 118.7 (C-3'), 142.3 (C-4), 143.5 (C-2'), 150.1 (C-4'), 164.3 (C-2), 172.8 (C = O), 124.2, 124.5, 126.3, 129.1, 133.4, 135.6, 137.9 (Aromatic carbons, C-5', C-2'' & C-4'') ppm. HRMS (m/z): 546.9713 [M + Na]+; Anal. Calcd. for C19H14ClN5O5S3:C, 43.55; H, 2.69; N, 13.37; Found: C, 43.48; H, 2.75; N, 13.45%.
N-(4-(4-Chlorothiophen-2-yl)thiazol-2-yl)-2-(N-(4-(4-nitrophenyl)-1H-pyrrol-2-yl)sulfamoyl) acetamide (9e) yield 68% ; m.p.: 155-157oC; IR (KBr): 3376 (CONH), 1728 (C = O), 1675 (C = C), 1579 (C = N), 1338 − 1145 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.38 (s, 2H, CH2), 6.63 (s, 1H, C3''-H), 7.10 (s, 1H, C5''-H), 7.21 (s, 1H, C5'-H), 7.68–7.84 (m, 6H, Ar-H, C3'-H & C5-H), 10.72 (bs,1H, NH), 11.08 (bs, 1H, CONH2), 12.06 (bs,1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 66.3 (H2C-CO), 105.8 (C-5), 107.7 (C-3''), 118.9 (C-5''), 121.8 (C-5'), 123.5 (C-3'), 146.1 (C-4), 150.4 (C-2'), 164.8 (C-2), 171.7 (C = O), 126.8, 128.4, 130.6, 133.0, 135.3, 136.5, 138.7 (Aromatic carbons, C-4', C-2'' & C-4'') ppm. HRMS (m/z): 546.9704 [M + Na]+; Anal. Calcd. for C19H14ClN5O5S3: C, 43.55; H, 2.69; N, 13.37; Found: C, 43.62; H, 2.64; N, 13.30 %.
2-(N-(4-(4-Nitrophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-nitrothiophen-2-yl)thiazol-2-yl) acetamide (9f) yield 70% ; m.p.: 170-172oC; IR (KBr): 3374 (CONH), 1714 (C = O), 1679 (C = C), 1571 (C = N), 1335 − 1139 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.33 (s, 2H,CH2), 6.78 (s, 1H, C3''-H), 7.23 (s, 1H, C5''-H), 7.72–7.84 (m, 5H, Ar-H & C5-H), 8.45 (s, 1H, C5'-H), 8.67 (s, 1H, C3'-H), 10.83 (bs,1H, NH), 11.21 (bs, 1H, CONH2), 12.15 (bs,1H, Pyrrole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 67.6 (H2C-CO), 107.2 (C-5), 108.3 (C-3''), 116.2 (C-5''), 119.2 (C-3'), 151.3 (C-4'), 165.3 (C-2), 172.9 (C = O), 128.1, 130.4, 132.8, 134.3, 135.4, 136.6, 138.0, 141.2, 142.7 (Aromatic carbons, C-4, C-2', C-5', C-2'' & C-4'') ppm. HRMS (m/z): 557.5261 [M + Na]+; Anal. Calcd. for C19H14N6O7S3: C, 42.69; H, 2.64; N, 15.72; Found: C, 42.61; H, 2.60; N, 15.64 %.
N-(4-(4-Chlorothiophen-2-yl)-1H-imidazol-2-yl)-2-(N-(4-phenyl-1H-pyrrol-2-yl)sulfamoyl) acetamide (10a) yield 69% ; m.p.: 159-161oC; IR (KBr): 3364 (CONH), 1668 (C = O), 1653 (C = C), 1565 (C = N), 1321 − 1134 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.26 (s, 2H, CH2), 6.57 (s, 1H, C3''-H), 7.02 (s, 1H, C5''-H), 7.25–7.60 (m, 7H, Ar-H, C3'-H & C5'-H), 7.75 (s, 1H, C5-H), 9.82 (bs, 1H, CONH2), 10.27 (bs, 1H, SO2NH), 11.40 (bs, 1H, Pyrrole NH), 12.45 (bs, 1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 66.1 (H2C-CO), 105.2 (C-3''), 117.5 (C-5''), 119.1 (C-5), 144.2 (C-2'), 153.2 (C-2), 169.6 (C = O), 122.8, 125.3, 126.7, 127.4, 128.6, 130.2, 132.1, 134.7, 136.8, 139.3 (Aromatic carbons, C-4, C-3', C-4', C-5', C-2'' & C-4'') ppm. HRMS (m/z): 484.9291 [M + Na]+; Anal. Calcd. for C19H16ClN5O3S2: C, 49.40; H, 3.49; N, 15.16; Found: C, 49.34; H, 3.55; N, 15.24 %.
N-(4-(4-Nitrothiophen-2-yl)-1H-imidazol-2-yl)-2-(N-(4-phenyl-1H-pyrrol-2-yl)sulfamoyl) acetamide (10b) yield 70% ; m.p.: 174-176oC; IR (KBr): 3365 (CONH), 1698 (C = O), 1642 (C = C), 1568 (C = N), 1328 − 1136 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.25 (s, 2H, CH2), 6.55 (s, 1H, C3''-H), 7.06 (s, 1H, C5''-H), 7.35–7.67 (m, 5H, Ar-H), 7.83 (s, 1H, C5-H), 8.41 (s, 1H, C5'-H), 8.80 (s, 1H, C3'-H), 10.28 (bs, 1H, CONH2), 10.60 (bs, 1H, NH), 11.46 (bs, 1H, Pyrrole NH), 12.53 (bs, 1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 64.9 (H2C-CO), 104.2 (C-3''), 116.4 (C-5''), 118.3 (C-3'), 120.2 (C-5), 144.1 (C-2'), 146.7 (C-4'), 153.5 (C-2), 171.9 (C = O), 125.6, 126.9, 129.3, 131.6, 133.2, 136.5, 138.3, 139.1 (C-4, C-5', C-2'', C-4'' & Aromatic carbons) ppm. HRMS (m/z): 495.4843 [M + Na]+; Anal. Calcd. for C19H16N6O5S2: 48.30; H, 3.41; N, 17.79; Found: C, C, 48.36; H, 3.47; N, 17.89 %.
2-(N-(4-(4-Chlorophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-chlorothiophen-2-yl)-1H-imidazol-2-yl)acetamide (10c) yield 69% ; m.p.: 185-187oC; IR (KBr): 3362 (CONH), 1676 (C = O), 1668 (C = C), 1571 (C = N), 1329 − 1125 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.28 (s, 2H, CH2), 6.54 (s, 1H, C3''-H), 7.05 (s, 1H, C5''-H), 7.18 (s, 1H, C5'-H), 7.55–7.80 (m, 6H, Ar-H, C3'-H & C5-H), 10.17 (bs, 1H, CONH2), 10.28 (bs, 1H, NH), 11.89 (bs, 1H, Pyrrole NH) 12.60 (bs,1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 64.8 (H2C-CO), 106.1 (C-3''), 117.5 (C-5''), 119.2 (C-5), 144.1 (C-2'), 153.8 (C-2), 170.1 (C = O), 122.2, 124.6, 126.7, 128.5, 130.5, 133.6, 135.4, 136.3, 137.1, 138.7 (Aromatic carbons, C-4, C-3', C-4', C-5', C-2'' & C-4'') ppm. HRMS (m/z): 519.3705 [M + Na]+; Anal. Calcd. for C19H15Cl2N5O3S2:C, 45.97; H, 3.05; N, 14.11; Found: C, 45.90; H, 3.00; N, 14.23%.
2-(N-(4-(4-Chlorophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-nitrothiophen-2-yl)-1H-imidazol-2-yl)acetamide (10d) yield 69% ; m.p.: 194-196oC; IR (KBr): 3361 (CONH), 1695 (C = O), 1637 (C = C), 1570 (C = N), 1331 − 1136 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.27 (s, 2H, CH2), 6.58 (s, 1H, C3''-H), 7.09 (s, 1H, C5''-H), 7.70–7.88 (m, 5H, Ar-H & C5-H), 8.41 (s, 1H, C5'-H), 8.78 (s, 1H, C3'-H), 10.38 (bs, 1H, CONH2), 10.56 (bs, 1H, NH), 11.86 (bs, 1H, Pyrrole NH), 12.59 (bs, 1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 64.2 (H2C-CO), 106.8 (C-3''), 116.2 (C-5''), 117.9 (C-3'), 119.5 (C-5), 144.6 (C-2'), 149.5 (C-4'), 153.6 (C-2), 170.2 (C = O), 123.7, 126.1, 128.9, 130.3, 134.2, 136.2, 137.1, 139.3 (Aromatic carbons, C-4, C-5', C-2'' & C-4'') ppm. HRMS (m/z): 529.9264 [M + Na]+; Anal. Calcd. for C19H15ClN6O5S2: C, 45.02; H, 2.98; N, 16.58; Found: C, 44.96; H, 2.91; N, 16.65 %.
N-(4-(4-Chlorothiophen-2-yl)-1H-imidazol-2-yl)-2-(N-(4-(4-nitrophenyl)-1H-pyrrol-2-yl) sulfamoyl)acetamide (10e) yield 72% ; m.p.: 183-185oC; IR (KBr): 3369 (CONH), 1718 (C = O), 1643 (C = C), 1580 (C = N), 1341 − 1138 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.35 (s, 2H, CH2), 6.68 (s, 1H, C3''-H), 7.07 (s, 1H, C5''-H), 7.16 (s, 1H, C5'-H), 7.42 (s, 1H, C3'-H), 7.56–7.78 (m, 5H, Ar-H & C5-H), 10.49 (bs, 1H, CONH2), 10.67 (bs, 1H, NH), 11.96 (bs, 1H, Pyrrole NH), 12.65 (bs, 1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 65.5 (H2C-CO), 106.6 (C-3''), 117.8 (C-5''), 145.8 (C-2'), 151.9 (C-2), 171.6 (C = O), 121.3, 124.6, 126.4, 127.1, 129.5, 131.1, 132.4, 133.6, 134.5, 135.9, 137.8 (Aromatic carbons, C-4, C-5, C-3', C-4', C-5', C-2'' & C-4'') ppm. HRMS (m/z): 529.9255 [M + Na]+; Anal. Calcd. for C19H15ClN6O5S2: C, 45.02; H, 2.98; N, 16.58; Found: C, 44.95; H, 3.03; N, 16.67%.
2-(N-(4-(4-Nitrophenyl)-1H-pyrrol-2-yl)sulfamoyl)-N-(4-(4-nitrothiophen-2-yl)-1H-imidazol-2-yl) acetamide (10f) yield 73% ; m.p.: 210-212oC; IR (KBr): 3378 (CONH), 1728 (C = O), 1667 (C = C), 1565 (C = N), 1329 − 1141 (SO2) (cm− 1); 1H NMR (400 MHz, DMSO-d6): δ 4.21 (s, 2H, CH2), 6.57 (s, 1H, C3''-H), 7.10 (s, 1H, C5''-H), 7.58–7.72 (m, 5H, Ar-H & C5-H), 8.28 (s, 1H, C5'-H), 8.73 (s, 1H, C3'-H), 10.43 (bs, 1H, CONH2), 10.60 (bs,1H, NH), 11.48 (bs,1H, Pyrrole NH), 12.54 (bs,1H, Imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ 66.2 (H2C-CO), 107.5 (C-3''), 116.2 (C-5''), 118.3 (C-3'), 121.5 (C-5), 149.8 (C-4'), 152.7 (C-2), 171.9 (C = O), 126.9, 128.4, 130.7, 133.7, 135.4, 137.8, 140.4, 142.6, 145.0 (Aromatic carbons, C-4, C-2', C-5', C-2'' & C-4'') ppm. HRMS (m/z): 540.4803 [M + Na]+; Anal. Calcd. for C19H15N7O7S2: C, 44.10; H, 2.92; N, 18.95; Found: C, 44.03; H, 2.97; N, 18.83 %.