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Reaktion von 3-Amino-2H-azirinen mit Diphenylcyclopropenthion. Vorläufige Mitteilung

✍ Scribed by Stanislav Chaloupka; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
201 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Reaction of 3‐Amino‐2__H__‐azirines with Diphenylcyclopropenethione

3‐Dimethylamino‐2__H__‐azirines (4a, 4b) react with diphenylcyclopropenethione (8) to give 4(3 H)‐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(3 H)‐pyridinethione 10a yields 2‐oxo‐2, 3‐dihydro‐4(1 H)‐pyridinethione (11) and reduction of 10a with sodium borohydride leads to the 2, 3‐dihydro‐4 (1 H)‐pyridinethione 12 (Scheme 4). The results of the reaction of 4a, 4b and the thione 8 demonstrate the 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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