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Syntheses of potentially bioactive [1,2,4]oxadiazolo[5,4‐ d ]benzothiazepines by 1,3‐dipolar cycloaddition
Author(s) -
Wu XiaoLong,
Liu FangMing,
Shen SongWei
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.479
Subject(s) - chemistry , cycloaddition , ring (chemistry) , 1,3 dipolar cycloaddition , dipole , combinatorial chemistry , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , catalysis
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).