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Synthesis of 1,2,5-Thiadiazepine Derivatives by Ring Enlargement of 1,2-Thiazetidin-3-one 1,1-Dioxides with 3-Amino-2H-azirines

✍ Scribed by Tonya R. Mihova; Anthony Linden; Heinz Heimgartner

Publisher: John Wiley and Sons
Year: 1996
Tongue: German
Weight: 474 KB
Volume: 79
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19960790803

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✦ Synopsis

Abstract

At 0° in MeCN, 2,2‐disubstituted 3‐amino‐2__H__‐azirines 1 and 4,4‐disubstituted 1,2‐thiazetidin‐3‐one 1,1‐dioxides 7 react smoothly to give 1,2,5‐thiadiazepin‐6‐one 1,1‐dioxides of type 8 (Scheme 2). The reaction mechanism of this regiospecific ring enlargement to seven‐membered heterocycles follows previously described pathways. The structures of 7a and 8b were established by X‐ray crystallography (see Figs. 1 and 2).

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