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Reaktion von 3-Amino-2H-azirinen mit Diphenylcyclopropenthion


Chaloupka, Stanislav; Heimgartner, Heinz (1979). Reaktion von 3-Amino-2H-azirinen mit Diphenylcyclopropenthion. Helvetica Chimica Acta, 62(1):86-89.

Abstract

Reaction of 3-Amino-2H-azirines with Diphenylcyclopropenethione : 3-Dimethylamino-2H-azirines (4a, 4b) react with diphenylcyclopropenethione (8) to give 4(3H)-pyridinethione derivatives of type 10 (Scheme 3). The reaction mechanism for the formation of 10 is given in Scheme 3 by analogy with a previous reported one [4] [5]. Hydrolysis of the 4(3H)-pyridinethione 10a yields 2-oxo-2,3-dihydro-4(1H)-pyridinethione (11) and reduction of 10a with sodium borohydride leads to the 2,3-dihydro-4(1H)-pyridinethione 12 (Scheme 4). The results of the reaction of 4a, 4b and the thione 8 demonstrate ihe similarity to the reaction of 4a, 4b and 2 [5] (cf. Scheme 1). In contrast, the reactions of imines of type 7a with 2 and 8, respectively, lead to different products (cf. [1][6]).

Reaction of 3-Amino-2H-azirines with Diphenylcyclopropenethione : 3-Dimethylamino-2H-azirines (4a, 4b) react with diphenylcyclopropenethione (8) to give 4(3H)-pyridinethione derivatives of type 10 (Scheme 3). The reaction mechanism for the formation of 10 is given in Scheme 3 by analogy with a previous reported one [4] [5]. Hydrolysis of the 4(3H)-pyridinethione 10a yields 2-oxo-2,3-dihydro-4(1H)-pyridinethione (11) and reduction of 10a with sodium borohydride leads to the 2,3-dihydro-4(1H)-pyridinethione 12 (Scheme 4). The results of the reaction of 4a, 4b and the thione 8 demonstrate ihe similarity to the reaction of 4a, 4b and 2 [5] (cf. Scheme 1). In contrast, the reactions of imines of type 7a with 2 and 8, respectively, lead to different products (cf. [1][6]).

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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:German
Date:1979
Deposited On:12 Aug 2014 16:08
Last Modified:05 Apr 2016 18:00
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Permanent URL: https://doi.org/10.5167/uzh-98033

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