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Selenium-containing heterocycles from isoselenocyanates: synthesis of 1,2,3-selenadiazole derivatives


Zhou, Yuehui; Heimgartner, Heinz (2000). Selenium-containing heterocycles from isoselenocyanates: synthesis of 1,2,3-selenadiazole derivatives. Helvetica Chimica Acta, 83:539-553.

Abstract

The reaction of aroyl chlorides 1 with KSeCN and ethyl diazoacetate (6) in acetone at room temperature yields ethyl 2-aroyl-5-(aroylimino)-2,5-dihydro-1,2,3-selenadiazole-4-carboxylates 7 (Scheme 3). A reaction mechanism via the initial formation of the corresponding aroyl isoselenocyanates 2 followed by a 1,3-dipolar cycloaddition of the diazo compound with the C=Se bond to give ethyl 5-(aroylimino)-4,5-dihydro-1,2,3-selenadiazole-4-carboxylates of type D is proposed. Acylation of the latter at N(2) leads to the final products 7. Deacetylation of 7 to give ethyl 5-(aroylimino)-1,2,3-selenadiazole-4-carboxylates 10 is achieved by treatment of 7 with morpholine (Scheme 5). The intermediate isoselenocyanates 2 partially oligomerize to give two different oligomers. The symmetrical one reacts with morpholine to yield selenourea derivatives 12 (Scheme 6).

The reaction of aroyl chlorides 1 with KSeCN and ethyl diazoacetate (6) in acetone at room temperature yields ethyl 2-aroyl-5-(aroylimino)-2,5-dihydro-1,2,3-selenadiazole-4-carboxylates 7 (Scheme 3). A reaction mechanism via the initial formation of the corresponding aroyl isoselenocyanates 2 followed by a 1,3-dipolar cycloaddition of the diazo compound with the C=Se bond to give ethyl 5-(aroylimino)-4,5-dihydro-1,2,3-selenadiazole-4-carboxylates of type D is proposed. Acylation of the latter at N(2) leads to the final products 7. Deacetylation of 7 to give ethyl 5-(aroylimino)-1,2,3-selenadiazole-4-carboxylates 10 is achieved by treatment of 7 with morpholine (Scheme 5). The intermediate isoselenocyanates 2 partially oligomerize to give two different oligomers. The symmetrical one reacts with morpholine to yield selenourea derivatives 12 (Scheme 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:English
Date:2000
Deposited On:29 Oct 2013 10:57
Last Modified:05 Apr 2016 17:05
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Dr. Helmut Legerlotz-Stiftung, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/(SICI)1522-2675(20000315)83:3<539::AID-HLCA539>3.0.CO;2-6
Permanent URL: https://doi.org/10.5167/uzh-83837

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