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. J. Chinese Universities ›› 2002, Vol. 23 ›› Issue (11): 2097.

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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

LIU Fang-Ming¹, WANG Bao-Lei², LI Yan-Ping¹

1. College of Chemistry and Chemical Engineering, Xinjiang University, Wulumuqi 830046, China;
2. Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China

Received:2001-07-17 Online:2002-11-24 Published:2002-11-24

Abstract

Abstract: Benzothiazepines containing 2-phenyl-1,2,3-triazole(2a-2e) which have potentially useful pharmacological properties were synthesized from α,β- unsaturated ketones(1a-1e) and 2-aminothiophenol, and then underwent 1,3-dipolar cycloaddition reaction with aryl nitrile oxides "in situ" and a series of 1,2,4-oxadiazolo benzothiazepine derivatives containing 2-phenyl-1,2,3-triazole(3a-3j) were obtained. The experimental results show that if the substituent R¹ or R² at phenyl of 1,5-benzothiazepine is electron-donated, it will facilitate the 1,3-dipolar cycloaddition reaction. The structures of the products were confirmed by IR, ¹H NMR, MS and elementary analyses, and their spectrum characters were also discussed.

Key words: Benzothiazepine, 2-Phenyl-1,2,3-triazole, 1,3-Dipolar cycloaddition, 1,2,4-Oxadiazole

CLC Number:

O626

TrendMD:

LIU Fang-Ming, WANG Bao-Lei, LI Yan-Ping . 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[J]. Chem. J. Chinese Universities, 2002, 23(11): 2097.

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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

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