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Paper | Regular issue | Vol 65, No. 11, 2005, pp.2705-2720
Published online, 13th September, 2005
DOI: 10.3987/COM-05-10530
Isothiazolo[3,2-b]-1,3,4-oxadiazole-5,5-dioxide: Synthesis of a New Heteropentalene System

Stephan Schmidt, Arne Kolberg, Lothar Hennig, Jens Hunger, and Bärbel Schulze*

*Department of Organic Chemistry, Leipzig University, Johannisallee 29, Leipzig 04103, Germany

Abstract

Monocyclic, acceptor-substituted N-aroylisothiazolium-2-imines (5a-d), easily available by cyclocondensation of 2-methyl-3-thiocyanato-2-butenal with aryl hydrazides, are described and the structure of new five-membered azomethine imines (5) is determined by X-Ray structure of 5a. The oxidation of 2-imines (5) with hydrogen peroxide in acetic acid gives 3-hydroperoxysultims (rac-cis 6) , -sultams (7), and 3-oxosultams (10). The 3-hydroxysultams (8a-d) are obtained by reduction of hydroperoxides (7). Surprisingly, after the dehydration of 8a-h and its 1,5-electrocyclization, a new type of heteropentalenes, the isothiazolo[3,2-b]-1,3,4-oxadiazole-5,5-dioxides (11) is formed.