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Selective synthesis of bis[1,2]dithiolo[1,4]thiazines from 4-isopropylamino-5-chloro-1,2-dithiole-3-ones

Konstantinova, Lidia S., Berezin, Andrej A., Lysov, Kirill A. and Rakitin, Oleg A. 2007. Selective synthesis of bis[1,2]dithiolo[1,4]thiazines from 4-isopropylamino-5-chloro-1,2-dithiole-3-ones. Tetrahedron Letters 48 (33) , pp. 5851-5854. 10.1016/j.tetlet.2007.06.071

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Reaction of 4-isopropylamino-5-chloro-1,2-dithiole-3-ones 3 and S2Cl2 in acetonitrile gave selectively 3-oxo-bis[1,2]dithiolo[1,4]thiazine-5-thiones 1 by the addition of triethylamine and bis[1,2]dithiolo[1,4]thiazine-3,5-diones 5 under the action of formic acid. 3,5-Diones 5 were also obtained by intramolecular cyclization of N,N-bis(5-chloro-3-oxo[1,2]dithiol-4-yl)amines 6 with S2Cl2 in the presence of Et3N.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Elsevier
ISSN: 0040-4039
Date of Acceptance: 14 June 2007
Last Modified: 20 Jan 2020 14:30

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