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Synthesis and Structure of a 1,2,5,7-Benzothiatriazonine


Schläpfer-Dähler, Marlise; Prewo, Roland; Bieri, Jost H; Heimgartner, Heinz (1984). Synthesis and Structure of a 1,2,5,7-Benzothiatriazonine. Heterocycles, 22:1667-1672.

Abstract

3-Dimethylamino-2,2-dimethyl-2H-azirine (1) and 4-phenyl-3,4-dihydro-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxide (6) react already below room temperature to give a nine-membered heterocyclic product, namely 3-dimethylamino-4,4-dimethyl-7-phenyl-4,5,6,7-tetrahydro-1,2,5,7-benzothiatriazonin-6-on-1,1-dioxide (7, Scheme 2) in a quantitative yield. The structure of this new heterocycle has been confirmed by X-ray crystallographic analysis (Fig. 1 and 2). In Scheme 2 a reaction mechanism for the formation of 1 is discussed, the zwitterion b being the key intermediate.

Abstract

3-Dimethylamino-2,2-dimethyl-2H-azirine (1) and 4-phenyl-3,4-dihydro-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxide (6) react already below room temperature to give a nine-membered heterocyclic product, namely 3-dimethylamino-4,4-dimethyl-7-phenyl-4,5,6,7-tetrahydro-1,2,5,7-benzothiatriazonin-6-on-1,1-dioxide (7, Scheme 2) in a quantitative yield. The structure of this new heterocycle has been confirmed by X-ray crystallographic analysis (Fig. 1 and 2). In Scheme 2 a reaction mechanism for the formation of 1 is discussed, the zwitterion b being the key intermediate.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1984
Deposited On:02 Jul 2014 14:34
Last Modified:08 Dec 2017 06:13
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche & Co. AG, Basel

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