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Syntheses of potentially bioactive [1,2,4]oxadiazolo[5,4-d]benzothiazepines by 1,3-dipolar cycloaddition

✍ Scribed by Xiao-Long Wu; Fang-Ming Liu; Song-Wei Shen

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
231 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image The chalcones, 2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h, 2i, 2j, 2k, 2l reacted with o‐aminobenzenthiol to give a series of 1,5‐benzothiazepines, 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l. The [3+2] 1, 3‐dipolar cycloaddition reactions of 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l with ethyl chlorooximidoacetate in the presence of Et~3~N afforded the target compounds, 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4l possessing an additional 1,2,4‐oxadiazole ring fused to the heptaatomic nucleus. The structures have been elucidated by spectral methods and X‐ray crystallographic analysis. J. Heterocyclic Chem., (2010).

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