Volume 24, Issue 14
Heterocyclic Compounds
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ChemInform Abstract: Ring-Enlargement Reaction Yielding 1,2,5-Benzothiadiazonin-6-one 1,1- Dioxides.

A. S. ORAHOVATS

A. S. ORAHOVATS

Org.-Chem. Inst., Univ. Zuerich, CH-8057 Zuerich, Switz.

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A. LINDEN

A. LINDEN

Org.-Chem. Inst., Univ. Zuerich, CH-8057 Zuerich, Switz.

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H. HEIMGARTNER

H. HEIMGARTNER

Org.-Chem. Inst., Univ. Zuerich, CH-8057 Zuerich, Switz.

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First published: April 6, 1993

Abstract

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ChemInform Abstract

Reaction of the NH-acidic benzothiazinone 1,1-dioxide (I) with azirines (II) in MeCN affords the nine-membered title heterocycles ( III) in fair to good yield. The structure of this novel type of heterocyclic systems is established by X-ray analysis of (IIIa). A ring expansion mechanism via a zwitterionic intermediate is proposed.

chemical structure image

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