, 1H NMR (400 MHz, d6-DMSO) H: 5.86 (s, 1H, proton at C-4), 7.23 (t, J = eight.72 Hz, 2H, aryl protons), 7.69 (dd, J = 8.30 and 7.23 Hz, 2H, aryl protons), 9.70 (bs, 1H, -NH proton), 12.00 (bs, 1H, -OH proton); 13C NMR (one hundred MHz, d6-DMSO): 86.71 (C-4), 115.52, 115.74, 126.82, 126.74 (aryl carbons), 160.41 (C-4), 162.84 (C-5). MS calculated for C9H7FN2O: 178.10. Located: 177.0 (M-1).Ragavan et al. Organic and Medicinal Chemistry Letters 2013, three:six http://orgmedchemlett/content/3/1/Page 11 of4-Methyl-3-phenyl-1H-pyrazol-5(4H)-one (four)3-Cyclohexyl-1H-pyrazol-5(4H)-one (8)Purified by recrystallisation utilizing ethanol (white solid), m.p: 218.five to 220.0 , 1H NMR (400 MHz, d6-DMSO) H: 1.99 (s, 3H, methyl protons at C-4), 7.34 (t, J = 7.20 Hz, 1H, para proton of aryl), 7.45 (t, J = eight.00 Hz, 2H, meta protons of aryl), 7.53 (d, J = eight.00 Hz, 2H, ortho protons of aryl), 9.50 (bs, 1H, -NH proton), 11.70 (bs, 1H, -OH proton); 13C NMR (100 MHz, d6-DMSO): 7.66 (methyl carbon at C-4), 95.98 (C-4), 126.31, 127.49, 128.78, 131.15 (aryl carbons), 139.54 (C-3), 160.28 (C-5). MS calculated for C10H10N2O: 174.19. Found: 173.0 (M-1).four,five,6,7-Tetrahydro-2H-indazol-3(3aH)-one (five)Purified by recrystallisation working with ethanol (white solid), m.p: 241.five to 243.0 , 1H NMR (400 MHz, d6-DMSO) H: 1.21 to 1.26 (m, 1H, proton of cyclohexyl ring), 1.29 to 1.34 (m, 4H, protons of cyclohexyl ring), 1.63 to 1.71 (m, 3H, protons of cyclohexyl ring), 1.84 to 1.90 (m, 2H, protons of cyclohexyl ring)), two.44 to 2.50 (m, 1H, proton at C1 of cyclohexyl ring), 5.20 (s, 1H, proton at C-4), 9.30 (bs, 1H, -NH proton), 11.00 (bs, 1H, -OH proton); 13 C NMR (100 MHz, d6-DMSO) : 25.97, 26.08, 32.66, 35.60 (carbons of cyclohexyl ring), 86.74 (C-4), 149.83 (C-3), 161.17 (C-5). MS calculated for C9H14N2O: 166.22. Identified: 166.9 (M+).3-(3-Chloropropyl)-1H-pyrazol-5(4H)-one (9)Purified by recrystallisation working with ethanol (white solid), m.p: 286.0 to 288.0 , 1H NMR (400 MHz, d6-DMSO) H: 1.66 to 1.59 (m, 4H, 4 protons of cyclohexane fused ring), two.21 (t, J = 5.20 Hz, 2H, two protons of cyclohexane fused ring), 2.42 (t, J = 6.0 Hz, 2H, two protons of cyclohexane fused ring), 9.95 (bs, 2H); 13C NMR (100 MHz, d6-DMSO): 19.35, 21.73, 22.74, 23.32 (carbons of fused cyclohexane element), 98.Formula of 1339559-21-5 88 (C-3 of pyrazole ring), 140.82409-02-7 structure 19 (C-4 of pyrazole ring), 158.PMID:24982871 87 (C-5 of pyrazole ring). MS calculated for C7H10N2O: 138.08. Identified: 138.16 (M+).3a,4,five,six,7,8-Hexahydrocyclohepta(e)pyrazol-3-(2H)-one (6)Purified by recrystallisation working with ethanol (white strong), m.p: 155.eight to 156.5 , 1H NMR (400 MHz, d6-DMSO) H: two.00 to 1.93 (m, 2H, methylene protons at C2 of propyl), 2.57 (t, J = 7.36 Hz, 2H, methylene protons at C1 of propyl), 3.62 (t, 6.40 Hz, 2H, methylene protons at C3 of propyl), 5.25 (s, 1H), 9.50 (bs, 1H, -NH proton), 11.20 (bs, 1H, -OH proton); 13C NMR (100 MHz, d6-DMSO): 23.51 (C2 of propyl), 37.18 (C1 of propyl), 45.13 (C3 of propyl), 88.56 (C-4), 143.39 (C-3), 161.20 (C-5). MS calculated for C6H9ClN2O: 160.60. Identified: 161.0 (M + 1 for Cl35) and 163.60 (M + 3 for Cl37).7-Methoxy-4,5-dihydro-2H-benzo(g)indazol-23(3aH)-one (10)Purified by recrystallisation working with ethanol (white solid), m.p: 220.five to 221.eight , 1H NMR (400 MHz, d6-DMSO) H: 1.56 to 1.50 (m, 4H, 4 protons of fused cycloheptane), 1.71 (d, J = five.52 Hz, 2H, two protons of fused cycloheptane), 2.29 (t, J = 5.60 Hz, 2H, two protons of fused cycloheptane), two.50 (t, J = 3.28 Hz, 2H, two protons of fused cycloheptane), 9.20 (bs, 1H, -NH proton), 11.00 (bs, 1H, -OH.
