Abstract
Reaction of 1,5-benzothiazepines, containing 2-phenyl-1,2,3-triazole 2a–d, with aryl nitrile oxides in CH2 Cl2 at room temperature leads to a series of novel 1,2,4-oxadiazolo[4,5-d]-1,5-benzothiazepine derivatives 3a-l in good yields. The products were characterized by IR, 1H NMR, MS, elemental analyses, X-ray and their spectrum characters were discussed.
Similar content being viewed by others
References
Kumari N, Saini RK, Joshi YC (2007) Synthesis of novel derivative of 1,5-benzothiazepines from 1,3-diketones and their antibacterial activity. Orient J Chem 23: 731–734
Fan B, Li J, Li Y, Yin S (2007) Synthesis and calm activity of 2-(4-β-D-allopyranosyloxyphenyl)-4-aryl-2,3-dihydro-1,5-benzothiazepine. Chin J Org Chem 27: 1150–1154
Pant S, Sharma P, Sharma A, Pant UC (2007) Synthesis of 1,5-benzothiazepines. Part XXXV. Synthesis and antimicrobial studies of 8-substituted-2-(2-chlorophenyl)-2,5-dihydro-4-(phenyl/1-naphthyl)-1,5-benzothiazepines. Indian J Heterocycl Chem 16: 345–348
Nikalje AP, Mane R, Ingle D (2006) Synthesis and antimicrobial activity of new 4-thiazolidinonyl-1,5-benzothiazepines. Int J Chem Sci 4: 145–150
Nikalje AG, Mane RA, Ingle DB (2006) Synthesis of new 1,5-benzothiazepines as prospective antimicrobial agents. Indian J Heterocycl Chem 15: 309–310
Shetgiri NP, Nayak BK (2003) Synthesis of some benzothiazepines and their antimicrobial activities. Indian J Chem B Org Chem 42: 683–687
Richard S (2005) Vascular effects of calcium channel antagonists: New evidence Drugs 65: 1–10. doi:10.2165/00003495-200565002-00002
Ansari FL, Umbreen S, Hussain L, Makhmoor T, Nawaz SA, Lodhi MA et al (2005) Syntheses and biological activities of chalcone and 1,5-benzothiazepine derivatives. Promising new free-radical scavengers, and esterase, urease, and α-glucosidase inhibitors. Chem Biodivers 2: 487–495. doi:10.1002/cbdv.200590029
Jiang L, Wan X, Xu H, Bian J, Han W, Zhu K et al (2007) Effect of diltiazem and lidocaine on arterial pressure or heart rate and the quality of extubation in patients undergoing uvulopalato-pharyngoplasty. J Med Coll PLA 22:230–233. doi:10.1016/S1000-1948(07)60046-X
Zhu S (2004) Canadian multicenter clentiazem angina trial. S Chin J Card Dis 10: 72
Xu F, Liu F, Shen L, Liu G, Yang C, Chen Q (2007) Synthesis and crystal structure of 2-p-methyloxyphenyl-3a-(2-phenyl-1,2,3-triazole-4-yl)-3,4-dihydro-1,2,4-oxa-diazolo[4,5-d] [1,5]benzothiazepine. Chin J Struct Chem 26: 1061–1065
Kamal A, Shankaraiah N, Devaiah V, Reddy KL, Juvekar A, Sen S et al (2008) Synthesis of 1,2,3-triazole-linked pyrrolobenzodiazepine conjugates employing ‘click’ chemistry: DNA-binding affinity and anticancer activity. Bioorg Med Chem Lett 18: 1468–1473. doi:10.1016/j.bmcl.2007.12.063
Zhu X, Chen X, Yan M, Shi D, Ding K (2008) Stereoselective synthesis and biological activities of O-(E)-1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethyleneamino-O-ethyl-O-arylphosphorothioates. Heteroatom Chem 19: 15–20. doi:10.1002/hc.20367
Aufort M, Herscovici J, Bouhours P, Moreau N, Girard C (2008) Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives. Bioorg Med Chem Lett 18: 1195–1198. doi:10.1016/j.bmcl.2007.11.111
Gallardo H, Conte G, Bryk F, Lourenco MCS, Costa MS, Ferreira VF (2007) Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent. J Braz Chem Soc 18: 1285–1291. doi:10.1590/S0103-50532007000600027
Liu F, Wang B, Li Y (2002) Synthesis of new 1,2,4-oxadiazolo[4,5-d][1,5] benzothiazepine derivatives containing 2-phenyl-1,2,3-triazole through 1,3-dipolar cycloaddition reaction. Chem Res Chin Univ 23: 2097–2101
Liu F, Wang B, Zhang Z, Sun W (2002) Synthesis of new 1,5-benzothiazepines containing 2-phenyl-1,2,3-triazole and their β-lactam derivatives. Acta Chimi Sin 60: 1095–1101
Chimirri A, Gitto R, Grasso S, Monforte P, Zappalà M (1994) 5H-[1,2,4]oxadiazolo[5,4-d][1,5]benzothiazepines: synthesis and stereo-chemistry. Heterocycles 38: 2289–2293
Yang D, Liu F, Xu F, Yang C (2008) Synthesis and crystal structure of compound 1,5-bis(4-methoxyphenyl)-3a-(2-phenyl-2H-1,2,3-triazol-4-yl)-4,5-dihydro-3aH-benzo[b][1,2,4]oxadiazolo[4,5-d][1,4]thiazepine. J Chem Crystallogr 38: 97–101. doi:10.1007/s10870-007-9269-7
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yang, DB., Liu, FM., Xu, F. et al. Synthesis and structure characterization of new 1,2,4-oxadiazolo[4,5-d]-1,5-benzothiazepines derivatives containing 2-phenyl-1,2,3-triazole through 1,3-dipolar cycloaddition reaction. Mol Divers 12, 103–109 (2008). https://doi.org/10.1007/s11030-008-9082-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-008-9082-z