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Synthesis of 1,3-Selenazol-2(3H)-imines


Atanassov, P K; Linden, A; Heimgartner, H (2010). Synthesis of 1,3-Selenazol-2(3H)-imines. Helvetica Chimica Acta, 93(3):395-404.

Abstract

The reaction of N,N’-diarylselenoureas 16 with phenacyl bromide in EtOH under reflux, followed by treatment with NH3 , gave N,3-diaryl-4-phenyl-1,3-selenazol-2(3H)-imines 13 in high yields (Scheme 2). A reaction mechanism via formation of the corresponding Se-(benzoylmethyl)isoselenoureas 18 and
subsequent cyclocondensation is proposed (Scheme 3). The N,N’-diarylselenoureas 16 were conveniently prepared by the reaction of aryl isoselenocyanates 15 with 4-substituted anilines. The structures of 13a and 13c were established by X-ray crystallography.

Abstract

The reaction of N,N’-diarylselenoureas 16 with phenacyl bromide in EtOH under reflux, followed by treatment with NH3 , gave N,3-diaryl-4-phenyl-1,3-selenazol-2(3H)-imines 13 in high yields (Scheme 2). A reaction mechanism via formation of the corresponding Se-(benzoylmethyl)isoselenoureas 18 and
subsequent cyclocondensation is proposed (Scheme 3). The N,N’-diarylselenoureas 16 were conveniently prepared by the reaction of aryl isoselenocyanates 15 with 4-substituted anilines. The structures of 13a and 13c were established by X-ray crystallography.

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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:11 March 2010
Deposited On:26 Mar 2010 14:08
Last Modified:05 Apr 2016 14:03
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.200900452

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