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Supporting Information
Regioselective synthesis of some new 1,4-disubstituted sulfonyl-1,2,3-triazoles and theirantibacterial activity studies
Narasimha Swamy Thirukovela1, Shravankumar Kankala1,*, Ranjith Kumar Kankala2, Suresh Paidakula1, Mohan Rao Gangula3, Chandra Sekhar Vasam4,* and Ravinder Vadde1,*
1Department of Chemistry, Kakatiya University, Warangal, Telangana State, India.
2Institute of Biotechnology, National Dong-Hwa University, Shou-Feng, Hualien 974, Taiwan, ROC.
3MedicinalChemistry Laboratory, Research Centre, C.K.M. Art’s & Science College, Warangal, Kakatiya University,Telangana State, India.
4Department of Pharmaceutical Chemistry, Telangana University, Nizamabad, Telangana State, India.
Corresponding Author Email Address: (S. Kankala)
(C. S. Vasam)
(R. Vadde)
General: All commercially available reagents were used without further purification. Reaction solvents were dried by standard methods before use. Purity of the compounds was checked by TLC using Merck 60F254 silica gel plates. Elemental analyses were obtained with an Elemental Analyser Perkin-Elmer 240C apparatus. 1H and 13C NMR spectra were recorded with a Mercuryplus 200 spectrometer (operating at400 MHz for 1H and 100 MHz for 13C); chemical shifts were referenced to TMS. EI (electron impact) mass spectra (at an ionising voltage of 70 eV) were obtained usinga Shimadzu QP5050A quadrupole-based mass spectrometer. IR spectra were recorded with a Perkin-Elmer 881 spectrometer.
General procedure for the synthesis of Sulfonyl-1,2,3-triazole hybrids (3a-f, 5a-i, 7a-d & 9a-e): Terminal alkyne (2, 4, 6 & 8) (0.055 mmol) was stirred in 5 ml of tertiary butanol and water (1:1 mixture). Copper sulphate (0.066 mmol) and sodium ascorbate (0.28 mmol) were charged into the reaction mixture. After 15 minutes, p-acetamidobenzenesulfonyl azide1 (0.055 mmol) was added to the above mixture and the reaction mass was allowed to stirr for 50 min, at which point it cleared and TLC analysis indicated complete consumption of the reactants. The reaction mixture was diluted with water extracted with DCM (2 x 20 ml). The combined organic layers were dried over anhydrous sodium sulphate and evaporated under reduced pressure to afford crude product, which was subjected to column chromatography (silica gel, 60-120 mesh, eluent; n-hexane/EtOAc gradient) to afford pure sulfonyl-1,2,3-triazoles (3a-f, 5a-h, 7a-d & 9a-e) in quantitative yields. The spectral data of all the products obtained is given as follows.
Spectral data of 3a-f, 5a-h, 7a-d & 9a-e:
N-(4-(4-Phenyl-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(3a)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s,-COCH3), 6.42-7.14 (5H, m, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.25 (1H, s, -NH), 8.42 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,): δ= 19.24, 119.84, 123.84, 124.82, 126.14, 130.42, 138.14, 142.54, 148.20, 150.10, 172.40 ppm. MS (EI, 70 eV): m/z (%) = 365 [M + Na]+. Anal.Calcd. for C16H14N4O3S: C, 56.13; H, 4.12; N, 16.36.Found: C, 56.09; H, 4.10; N, 16.32.
N-(4-(4-(4-Methoxyphenyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (3b)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 3.45 (3H, s, -OCH3), 6.65 (2H, d, J = 7.8 Hz, Ar-H), 7.73 (2H, d, J = 8.6 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.24 (1H, s,-NH), 8.41 (1H, s,triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,): δ= 19.24, 52.34, 115.20, 119.80, 124.80, 126.10, 138.14, 142.54, 148.20, 150.10, 152.42, 172.40 ppm. MS (EI, 70 eV): m/z (%) = 395 [M + Na]+. Anal. Calcd. for C17H16 N4O4S: C, 54.83; H, 4.33; N, 15.04.Found: C, 54.80; H, 4.32; N, 14.94.
N-(4-(4-(4-Chlorophenyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(3c)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 6.68 (2H, d, J = 7.8 Hz, Ar-H), 7.70 (2H, d, J = 8.6 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.24 (1H, s, -NH), 8.40 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,): δ= 19.24, 115.24, 119.84, 124.80, 126.10, 138.14, 142.52, 148.20, 150.10, 152.42, 172.40 ppm. MS (EI, 70 eV): m/z (%) = 399 [M + Na]+. Anal.Calcd. for C16H13ClN4O3S: C, 51.00; H, 3.48; N, 14.87.Found: C, 49.88; H, 3.46; N, 14.85.
N-(4-(4-p-Tolyl-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(3d)
1H-NMR (CDCl3, 400 MHz,): δ = 2.10 (3H, s,-CH3), 2.12 (3H, s, -COCH3), 6.62 (2H, d, J = 7.8 Hz, Ar-H), 7.72 (2H, d, J = 8.6 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.26 (1H, s, -NH), 8.42 (1H,s,triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,): δ= 19.25, 24.45, 115.20, 119.82, 124.82, 126.10, 138.15, 142.50, 148.20, 150.10, 152.40, 172.42 ppm. MS (EI, 70 eV): m/z (%) = 379 [M + Na]+. Anal. Calcd. for C17H16 N4O3S: C, 57.29; H, 4.52; N, 15.72.Found. C, 57.28; H, 4.50; N, 15.70.
N-(4-(4-(4-tert-Butylphenyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(3e)
1H-NMR (CDCl3, 400 MHz,): δ = 0.94 (9H, s, -C(CH3)3), 2.12 (3H, s, -COCH3), 6.81 (2H, d, J = 7.8 Hz, Ar-H), 7.76 (2H, d, J = 8.6 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.25 (1H, s, -NH), 8.42 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 32.86, 36.52, 115.20, 119.84, 124.80, 126.10, 138.14, 142.54, 148.20, 150.10, 152.42, 172.40 ppm. MS (EI, 70 eV): m/z (%) = 421 [M + Na]+. Anal.Calcd. for C20H22 N4O3S: C, 60.28; H, 5.56; N, 14.06.Found. C, 60.26; H, 5.52; N, 14.02.
N-(4-(4-(4-Cyanophenyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(3f)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 6.85 (2H, d, J = 7.8 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 7.94 (2H, d, J = 8.6 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.25 (1H, s, -NH), 8.42 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.22, 115.20, 119.84, 120.54, 124.82, 126.12, 138.15, 142.54, 148.20, 150.10, 152.42, 172.38 ppm. MS (EI, 70 eV): m/z (%) = 390 [M + Na]+. Anal.Calcd. for C17H13 N5O3S: C, 55.58; H, 3.57; N, 19.06.Found. C, 55.56; H, 3.55; N, 19.04.
N-(4-(4-p-Tolyloxymethyl-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(5a)
1H-NMR (CDCl3, 400 MHz,): δ = 2.10 (3H, s, -CH3), 2.12 (3H, s, -COCH3), 5.32 (2H, s, -CH2-O), 6.80 (2H, d, J = 7.2 Hz, Ar-H), 7.45 (2H, d, J = 8.4 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.28 (1H, s, -NH), 8.44 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3,100 MHz,): δ= 19.24, 24.20, 75.42, 115.20, 119.84, 124.82, 126.10, 130.45, 138.14, 140.10, 142.54, 148.26, 150.12, 172.42 ppm. MS (EI, 70 eV): m/z (%) = 409 [M + Na]+. Anal. Calcd. for C18H18 N4O4S: C, 55.95; H, 4.70; N, 14.50.Found. C, 55.92; H, 4.65; N, 14.48.
N-(4-(4-Phenoxymethyl-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(5b)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 5.32 (2H, s, -CH2-O), 6.42-7.26 (5H, m, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.26 (1H, s, -NH), 8.44 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 75.35, 119.83, 120.21, 123.84, 124.86, 126.14, 130.44, 138.14, 142.55, 148.20, 150.10, 172.45 ppm. MS (EI, 70 eV): m/z (%) = 395 [M + Na]+. Anal. Calcd. for C17H16 N4O4S: C, 54.83; H, 4.33; N, 15.04.Found. C, 54.80; H, 4.32; N, 14.94.
N-(4-(4-(4-Methoxyphenoxymethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(5c)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 3.45 (3H, s, -OCH3), 5.34 (2H, s, -CH2-O), 6.65 (2H, d, J = 7.6 Hz, Ar-H), 7.78 (2H, d, J = 8.2 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.26 (1H, s, -NH), 8.42 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 54.14, 75.38, 119.84, 121.54, 123.84, 124.82, 126.14, 130.42, 138.15, 142.54, 148.20, 150.12, 172.40 ppm. MS (EI, 70 eV): m/z (%) = 425 [M + Na]+. Anal. Calcd. for C18H18 N4O5S: C, 53.72; H, 4.51; N, 13.92. Found. C, 53.70; H,4.48; N, 13.90.
N-(4-(4-(4-Formylphenoxymethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (5d)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 5.34 (2H, s, -CH2-O), 6.65 (2H, d, J = 7.6 Hz, Ar-H), 7.78 (2H, d, J = 8.2 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.26 (1H, s, -NH), 8.42 (1H, s, triazole-H), 9.58 (1H, s, -CHO) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 75.34, 119.84, 120.21, 122.12, 123.84, 124.82, 126.14, 130.45, 138.14, 142.54, 148.20, 150.10, 165.26, 172.44 ppm. MS (EI, 70 eV): m/z (%) = 423 [M + Na]+. Anal. Calcd. for C18H16 N4O5S: C, 53.99; H, 4.03; N, 13.99.Found. C, 53.96; H, 4.00; N, 13.96.
N-(4-(4-(3-Chlorophenoxymethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (5e)
1H-NMR (CDCl3, 400 MHz,):δ = 2.12 (3H, s, -COCH3), 5.32 (2H, s, -CH2-O), 6.40-7.58 (4H, m, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.28 (1H, s, -NH), 8.43 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 75.38, 119.82, 120.21, 122.42, 124.82, 126.14, 130.42, 138.14, 142.54, 148.20, 150.12, 172.42 ppm. MS (EI, 70 eV): m/z (%) = 429 [M + Na]+. Anal. Calcd. for C17H15ClN4O4S: C, 50.19; H, 3.72; N, 13.77.Found. C, 50.18; H, 3.70; N, 13.75.
N-(4-(4-o-Tolyloxymethyl-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (5f)
1H-NMR (CDCl3, 400 MHz,): δ = 2.06 (3H, s, -CH3), 2.12 (3H, s, -COCH3), 5.32 (2H, s, -CH2-O), 6.80 (4H, m, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.26 (1H, s, -NH), 8.44 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 24.82, 75.38, 119.84, 120.21, 123.84, 124.82, 126.10, 130.42, 138.14, 142.54, 148.25, 150.10, 172.42 ppm. MS (EI, 70 eV): m/z (%) = 409 [M + Na]+. Anal. Calcd. for C18H18N4O4S: C, 55.95; H, 4.70; N, 14.50.Found. C, 55.92; H, 4.68; N, 14.48.
N-(4-(4-(4-Acetylphenoxymethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (5g)
1H-NMR (CDCl3, 400 MHz,): δ = 2.08 (3H, s, 4-acetyl), 2.12 (3H, s, -COCH3), 5.32 (2H, s, -CH2-O), 6.80 (2H, d, J = 6.5 Hz, Ar-H), 7.45 (2H, d, J = 8.2 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.26 (1H, s, -NH), 8.44 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 23.47, 75.35, 119.84, 120.21, 123.84, 124.86, 126.14, 130.42, 138.14, 142.54, 148.20, 150.18, 160.52, 172.39 ppm. MS (EI, 70 eV): m/z (%) = 437 [M + Na]+. Anal. Calcd. for C19H18 N4O5S: C, 55.06; H, 4.38; N, 13.52.Found. C, 55.04; H, 4.35; N, 13.50.
N-(4-(4-(4-Nitrophenoxymethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (5h)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 5.34 (2H, s, -CH2-O), 6.94 (2H, d, J = 7.6 Hz, Ar-H), 7.82 (2H, d, J = 7.2 Hz, Ar-H), 8.02 (2H, d, J = 8.1 Hz, Ar-H), 8.10 (2H, d, J = 8.2 Hz, Ar-H), 8.28 (1H, s, -NH), 8.44 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ= 19.24, 75.38, 119.84, 123.85, 124.80, 126.14, 130.42, 138.15, 142.54, 148.20, 150.10, 154.25, 172.45 ppm. MS (EI, 70 eV): m/z (%) = 440 [M + Na]+. Anal. Calcd. for C17H15N5O6S: C, 48.92; H, 3.62; N, 16.78.Found. C, 48.90; H, 3.60; N, 16.75.
N-(4-(4-(2-(2,4-Dinitrophenylsulfanyl)-benzoimidazol-1-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (7a)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 4.56 (2H, s, -CH2-N-benzimidazole), 6.94 (2H, d, Ar-H), 7.32-7.53 (4H, m, Ar-H), 7.79 (1H, d, J =7.5 Hz, Ar-H), 7.82 (2H, d, Ar-H), 8.26 (1H, s, -NH), 8.39 (1H, d, J = 7.5 Hz), 8.42 (1H, s, triazole-H), 8.84 (1H, s, Ar-H) ppm.13C-NMR (CDCl3, 100 MHz,):δ = 24.82, 50.42, 116.35, 118.42, 120.62, 122.32, 126.80, 128.25, 130.80, 132.80, 134.44, 137.12, 141.35, 142.34, 143.42, 144.25, 146.62, 150.20, 169.24ppm.MS (EI, 70 eV): m/z (%) = 595 [M + H]+. Anal. Calcd. for C24H18 N8O7S2: C, 48.48; H, 3.05; N, 18.85. Found. C, 48.46; H, 3.02; N, 18.84.
N-(4-(4-(5-Bromo-2-(2,4-dinitrophenylsulfanyl)-benzoimidazol-1-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (7b)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 4.56 (2H, s, -CH2-N-benzimidazole), 6.94 (2H, d, Ar-H), 7.13 (1H, d, J =6.5 Hz, Ar-H), 7.50 (1H, s, Ar-H), 7.79 (1H, d, J =7.5 Hz, Ar-H), 7.81(1H, d, J =6.5 Hz, Ar-H), 7.92 (2H, d, Ar-H), 8.25 (1H, s, -NH), 8.39 (1H, d, J = 7.5 Hz), 8.42 (1H, s, triazole-H), 8.78 (1H, s, Ar-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ = 24.82, 50.42, 116.35, 118.42, 120.62, 124.56, 126.80, 128.22, 130.80, 132.80, 134.45, 137.12, 141.35, 142.34, 143.42, 144.25, 146.62, 150.20, 169.21ppm. MS (EI, 70 eV): m/z (%) = 672 [M + H]+. Anal. Calcd. for C24H17 BrN8O7S2: C, 42.80; H, 2.54; N, 16.64.Found. C, 42.78; H, 2.52; N, 16.62.
N-(4-(4-(2-(2,4-Dinitrophenylsulfanyl)-5-methoxybenzoimidazol-1-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (7c)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 3.82 (3H, s, -OCH3), 4.56 (2H,s,-CH2-N-benzimidazole), 6.94 (2H, d, Ar-H), 7.13 (1H, d, J =6.5 Hz, Ar-H), 7.50 (1H, s, Ar-H), 7.79 (1H, d, J =7.5 Hz, Ar-H), 7.81(1H, d, J =6.5 Hz, Ar-H), 7.92 (2H, d, Ar-H), 8.28 (1H, s, -NH), 8.39 (1H, d, J = 7.5 Hz), 8.42 (1H, s, triazole-H), 8.78 (1H, s, Ar-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ = 24.82, 50.42, 58.40, 116.35, 118.42, 120.62, 124.15, 126.80, 128.25, 130.80, 132.80, 134.44, 137.12, 141.35, 142.34, 143.42, 144.25, 146.62, 150.20, 169.22ppm. MS (EI, 70 eV): m/z (%) = 625 [M + H]+. Anal. Calcd. for C25H20N8O8S2: C, 48.07; H, 3.23; N, 17.94.Found. C, 48.04; H, 3.22; N, 17.92.
N-(4-(4-(2-(2,4-Dinitrophenylsulfanyl)-5-nitrobenzoimidazol-1-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (7d)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 4.56 (2H, s, -CH2-N-benzimidazole), 6.94 (2H, d, Ar-H), 7.50 (1H, s, Ar-H), 7.56 (1H, d, J =8.2 Hz, Ar-H), 7.79 (1H, d, J =7.5 Hz, Ar-H), 7.92 (2H, d, Ar-H), 8.14 (1H, d, J = 8.2 Hz, Ar-H), 8.28 (1H, s, -NH), 8.39 (1H, d, J = 7.5 Hz), 8.42 (1H, s, triazole-H), 8.78 (1H, s, Ar-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ = 24.82, 50.42, 116.35, 118.42, 120.62, 126.80, 128.25, 130.80, 132.80, 134.44, 137.12, 141.35, 142.34, 143.42, 144.25, 146.62, 149.22, 150.20, 169.20 ppm. MS (EI, 70 eV): m/z (%) = 640 [M + H]+. Anal. Calcd. for C24H17N9O9S2: C, 45.07; H, 2.68; N, 19.71.Found. C, 45.05; H, 2.65; N, 19.70.
N-(4-(4-Benzo-4,5-imidazo-(2,1-a)-isoindol-5-ylmethyl-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (9a)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 4.56 (2H, s, -CH2-N-isoindole), 6.98-7.62 (13H, m, Ar-H), 8.26 (1H, s, -NH), 8.46 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ = 21.54, 50.64, 116.10, 121.62, 122.12, 124.10, 126.20, 128.25, 131.25, 132.80, 134.44, 137.12, 143.42, 168.60 ppm. MS (EI, 70 eV): m/z (%) = 485 [M + H]+. Anal. Calcd. for C25H20N6O3S: C, 61.97; H, 4.16; N, 17.34.Found. C, 61.95; H, 4.14; N, 17.32.
N-(4-(4-(8-Bromobenzo-4,5-imidazo-(2,1-a)-isoindol-5-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (9b)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 4.56 (2H, s, -CH2-N-isoindole), 6.97-7.64 (12H, m, Ar-H), 8.25 (1H, s, -NH), 8.46 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ = 21.54, 50.64, 116.14, 121.62, 122.15, 124.10, 126.20, 128.25, 131.25, 132.80, 134.45, 137.12, 143.42, 168.62ppm. MS (EI, 70 eV): m/z (%) = 563 [M + H]+. Anal. Calcd. for C25H19BrN6O3S: C, 53.29; H, 3.40; N, 14.92.Found. C, 53.25; H, 3.38; N, 14.90.
N-(4-(4-(8-Methoxybenzo-4,5-imidazo-(2,1-a)-isoindol-5-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (9c)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 3.82 (3H, s, -OCH3), 4.56 (2H, s, -CH2-N-isoindole), 6.85-7.60 (12H, m, Ar-H), 8.25 (1H, s, -NH), 8.46 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,): δ = 21.54, 50.64, 58.62, 116.10, 121.62, 122.12, 124.10, 126.20, 128.25, 131.25, 132.85, 134.44, 137.12, 143.42, 168.61ppm. MS (EI, 70 eV): m/z (%) = 515 [M + H]+. Anal. Calcd. for C26H22N6O4S: C, 60.69; H, 4.31; N, 16.33.Found. C, 60.65; H, 4.30; N, 16.30.
N-(4-(4-(8-Chlorobenzo-4,5-imidazo-(2,1-a)-isoindol-5-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide (9d)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 4.56 (2H, s, -CH2-N-isoindole), 6.97-7.64 (12H, m, Ar-H), 8.26 (1H, s, -NH), 8.46 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3, 100 MHz,):δ = 21.54, 50.65, 116.14, 121.62, 122.15, 124.10, 126.20, 128.20, 131.25, 132.80, 134.44, 137.12, 143.42, 168.56ppm. MS (EI, 70 eV): m/z (%) = 519 [M + H]+. Anal. Calcd. for C25H19ClN6O3S: C, 57.86; H, 3.69; N, 16.19.Found. C, 57.84; H, 3.68; N, 16.17.
N-(4-(4-(8-Methylbenzo-4,5-imidazo-(2,1-a)-isoindol-5-ylmethyl)-1,2,3-triazole-1-sulfonyl)phenyl)acetamide(9e)
1H-NMR (CDCl3, 400 MHz,): δ = 2.12 (3H, s, -COCH3), 2.54 (3H, s, -CH3), 4.56 (2H, s, -CH2-N-isoindole), 6.97-7.64 (12H, m, Ar-H), 8.26 (1H, s, -NH), 8.46 (1H, s, triazole-H) ppm. 13C-NMR (CDCl3,100 MHz,): δ = 21.54, 25.74, 50.66, 116.10, 121.62, 122.18, 124.10, 126.20, 128.25, 131.26, 132.82, 134.44, 137.12, 143.42, 168.62ppm. MS (EI, 70 eV): m/z (%) = 499 [M + H]+. Anal.Calcd. for C26H22N6O3S: C, 62.64; H, 4.45; N, 16.86.Found. C, 62.62; H, 4.42; N, 16.84.