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[3+2]-Cycloadditions of nitrilimines with heteroaryl thioketones


Ali, Korany A; Mloston, Grzegorz; Urbaniak, Katarzyna; Linden, Anthony; Heimgartner, Heinz (2017). [3+2]-Cycloadditions of nitrilimines with heteroaryl thioketones. Journal of Sulfur Chemistry:Epub ahead of print.

Abstract

The in situ generated nitrilimines are trapped efficiently with heteroaryl thioketones bearing thiophen-2-yl or selenophen-2-yl substituents. The exclusive products observed in these reactions are 2,3-dihydro-1,3,4-thiadiazoles formed via regioselective [3+2]-cycloaddition. Competitive head-to-tail dimerization of the intermediate 1,3-dipoles was not observed in any of the studied reactions.

Abstract

The in situ generated nitrilimines are trapped efficiently with heteroaryl thioketones bearing thiophen-2-yl or selenophen-2-yl substituents. The exclusive products observed in these reactions are 2,3-dihydro-1,3,4-thiadiazoles formed via regioselective [3+2]-cycloaddition. Competitive head-to-tail dimerization of the intermediate 1,3-dipoles was not observed in any of the studied reactions.

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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:2017
Deposited On:06 Jul 2017 13:34
Last Modified:07 Jul 2017 09:28
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:National Science Center (Cracow, Poland); Grant Maestro-3 (Dec-2012/06/A/ST5/00219), National Research Center Egypt
Additional Information:This is an Accepted Manuscript of an article published by Taylor & Francis in Journal of Sulfur Chemistry on 2017, available online: http://wwww.tandfonline.com/10.1080/17415993.2017.1346103.
Publisher DOI:https://doi.org/10.1080/17415993.2017.1346103

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