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Selenium-containing heterocycles from isoselenocyanates:5-methylselenazole derivatives from the reaction with malononitrile and propargyl chloride


Sommen, G L; Linden, A; Heimgartner, H (2008). Selenium-containing heterocycles from isoselenocyanates:5-methylselenazole derivatives from the reaction with malononitrile and propargyl chloride. Helvetica Chimica Acta, 91(2):209-219.

Abstract

Aryl isoselenocyanates 1 react with malononitrile (6a) and propargylchloride (8) in DMF in the presence of Et3N to give the corresponding 2-(3-aryl-2,3-dihydro-4-methyl-1,3-selenazol-2-ylidene)malononitriles 12 as major products. The analogous reaction takes place with benzoylacetonitrile (6b) instead of 6a. In some cases, the corresponding non-cyclic 2-[(arylamino)(prop-2-ynylselanyl)methylidene]malononitriles 9 were obtained as minor products. The structures of 9e and 11a have been established by X-ray crystallography.

Abstract

Aryl isoselenocyanates 1 react with malononitrile (6a) and propargylchloride (8) in DMF in the presence of Et3N to give the corresponding 2-(3-aryl-2,3-dihydro-4-methyl-1,3-selenazol-2-ylidene)malononitriles 12 as major products. The analogous reaction takes place with benzoylacetonitrile (6b) instead of 6a. In some cases, the corresponding non-cyclic 2-[(arylamino)(prop-2-ynylselanyl)methylidene]malononitriles 9 were obtained as minor products. The structures of 9e and 11a have been 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:February 2008
Deposited On:06 Feb 2009 09:57
Last Modified:05 Apr 2016 12:57
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Legerlotz Stiftung
Publisher DOI:https://doi.org/10.1002/hlca.200890025

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