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

• Published in: Journal of heterocyclic chemistry Vol. 47; no. 6; pp. 1350 - 1355
• Main Authors: Wu, Xiao-Long, Liu, Fang-Ming, Shen, Song-Wei
• Format: Journal Article
• Language: English
• Published: Hoboken, USA John Wiley & Sons, Inc 01.11.2010; Wiley
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; DRUG; 2-PHENYL-1,2,3-TRIAZOLE; (-)-CIS-2,3-DIHYDRO-3-(4-METHYLPIPERAZINYLMETHYL)-2-PHENYL-1,5-BENZOTHIAZEPIN-4 HYDROCHLORIDE BTM-1086; DOGS; DILTIAZEM; INHIBITORS; 1,5-BENZOTHIAZEPINE CALCIUM-ANTAGONIST; DERIVATIVES
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.479

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 Et3N 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).