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Reaktion von 3-(Dimethylamino)-2H-azirinen mit 1,3-Thiazolidin-2-thion


Ametamey, Simon M; Prewo, Roland; Bieri, Jost H; Heimgartner, Heinz; Obrecht, Jean-Pierre (1986). Reaktion von 3-(Dimethylamino)-2H-azirinen mit 1,3-Thiazolidin-2-thion. Helvetica Chimica Acta, 69(8):2013-2025.

Abstract

Reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-thiazolidine-2-thione (6) in MeCN at room temperature leads to a mixture of perhydroimidazo[4,3-b]thiazole-5-thiones 7 and N-[1-(4,5-dihydro-1,3-thiazol-2-yl)alkyI]-N',N'-dimethylthioureas 8 (Scheme 2), whereas, in i-PrOH at ca. 60°, 8 is the only product (Scheme 4). It has been shown that, in polar solvents or under Me2NH catalysis, the primarily formed 7 isomerizes to 8 (Scheme 4). The hydrolysis of 7 and 8 leads to the same 2-thiohydantoine 9 (Schemes 3 and 5). The structure of 7a, 8c, and 9b has been established by X-ray crystallography (Chapt. 4). Reaction mechanisms for the formation and the hydrolysis of 7 and 8 are suggested.

Reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-thiazolidine-2-thione (6) in MeCN at room temperature leads to a mixture of perhydroimidazo[4,3-b]thiazole-5-thiones 7 and N-[1-(4,5-dihydro-1,3-thiazol-2-yl)alkyI]-N',N'-dimethylthioureas 8 (Scheme 2), whereas, in i-PrOH at ca. 60°, 8 is the only product (Scheme 4). It has been shown that, in polar solvents or under Me2NH catalysis, the primarily formed 7 isomerizes to 8 (Scheme 4). The hydrolysis of 7 and 8 leads to the same 2-thiohydantoine 9 (Schemes 3 and 5). The structure of 7a, 8c, and 9b has been established by X-ray crystallography (Chapt. 4). Reaction mechanisms for the formation and the hydrolysis of 7 and 8 are suggested.

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Additional indexing

Other titles:Reaction of 3-(Dimethylamino)-2H-azirines with 1,3-Thiazolidine-2-thione
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1986
Deposited On:03 Jun 2014 07:01
Last Modified:05 Apr 2016 17:54
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19860690825
Permanent URL: https://doi.org/10.5167/uzh-96275

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