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An Efficient Procedure for the Preparation of 3-Acetyl-2,3-dihydrobenzo-thiazoles by Ring Contraction of 2,4-Diaryl-2,3-dihydro-1,5-benzothiazepines under Acetylating Conditions

✍ Scribed by Tóth, Gábor ;Lévai, Albert ;Balázs, Barbara ;Simon, András

Book ID: 102365980
Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 351 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970530

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✦ Synopsis

Abstract

Reaction of 2,4‐diaryl‐2,3‐dihydro‐1,5‐benzothiazepines 1 with a mixture of acetic anhydride and pyridine afforded 3‐acetyl‐2,3‐dihydrobenzothiazoles 2 as sole products in good yields. Stereochemistry and the hindered rotation of the amide group were studied by means of NMR spectroscopy and the results were corroborated by AM1 calculations. A reaction mechanism for the ring contraction is proposed.

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