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N-(1,3-Thiazol-5(4H)-yliden)amine aus 1,3-dipolaren Cycloadditionen von Aziden mit 1,3-Thiazo1-5(4H)-thionen


Pekcan, Sare; Heimgartner, Heinz (1988). N-(1,3-Thiazol-5(4H)-yliden)amine aus 1,3-dipolaren Cycloadditionen von Aziden mit 1,3-Thiazo1-5(4H)-thionen. Helvetica Chimica Acta, 71(7):1673-1680.

Abstract

Organic azides 5 and 4,4-dimethyl-2-phenyI-1,3-thiazol-5(4H)-thione (2) in toluene at 90° react to give the corresponding N-(1,3-thiazol-5(4H)-ylidene)amines ( = 1,3-thiazol-5(4H)-imines) 6 in good yield (Table). A reaction mechanism for the formation of these scarcely investigated thiazole derivatives is formulated in Scheme 3: 1,3-Dipolar azide cycloaddition onto the C=S group of 2 leads to the 1:1 adduct C. Successive elimination of N2 and S yields 6, probably via an intermediate thiaziridine E.

Abstract

Organic azides 5 and 4,4-dimethyl-2-phenyI-1,3-thiazol-5(4H)-thione (2) in toluene at 90° react to give the corresponding N-(1,3-thiazol-5(4H)-ylidene)amines ( = 1,3-thiazol-5(4H)-imines) 6 in good yield (Table). A reaction mechanism for the formation of these scarcely investigated thiazole derivatives is formulated in Scheme 3: 1,3-Dipolar azide cycloaddition onto the C=S group of 2 leads to the 1:1 adduct C. Successive elimination of N2 and S yields 6, probably via an intermediate thiaziridine E.

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Additional indexing

Other titles:N-(1,3-Thiazol-5(4H)-ylidene)amines via 1,3-Dipolar Cycloaddition of Azides and 1,3-Thiazol-5(4H)-thiones
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1988
Deposited On:14 May 2014 08:46
Last Modified:05 Apr 2016 17:49
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19880710713

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