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[2+3] Cycloadditions of Azomethine Ylides with 1,3-Thiazole-5(4H)-thiones


Mloston, Grzegorz; Linden, Anthony; Heimgartner, Heinz (1998). [2+3] Cycloadditions of Azomethine Ylides with 1,3-Thiazole-5(4H)-thiones. Helvetica Chimica Acta, 81(3-4):558-569.

Abstract

Thermal reactions of 1,2,3-trisubstituted ariridines 1 with 1,3-thiazole-5(4H)-thiones 6 in toluene yielded, in general, a mixture of two diastereoisomeric spirocyclic [2+3] cycloadducts. The formation of these products can be explained by a stereoselective electrocyclic ring opening of 1 to give an azomethine ylide 2 as the reactive intermediate, which is trapped immediately by 6 via a stereoselective 1,3-dipolar cycloaddition. Only in the case of trans-dimethyl 1-(4-methoxyphenyl)aziridine-2,3-dicarboxylate (trans-la), four diastereoisomeric cycloadducts were formed (Scheme 4). This result is rationalized by an isomerization of the intermediate azomethine ylide cis-2a to trans-2a.

Abstract

Thermal reactions of 1,2,3-trisubstituted ariridines 1 with 1,3-thiazole-5(4H)-thiones 6 in toluene yielded, in general, a mixture of two diastereoisomeric spirocyclic [2+3] cycloadducts. The formation of these products can be explained by a stereoselective electrocyclic ring opening of 1 to give an azomethine ylide 2 as the reactive intermediate, which is trapped immediately by 6 via a stereoselective 1,3-dipolar cycloaddition. Only in the case of trans-dimethyl 1-(4-methoxyphenyl)aziridine-2,3-dicarboxylate (trans-la), four diastereoisomeric cycloadducts were formed (Scheme 4). This result is rationalized by an isomerization of the intermediate azomethine ylide cis-2a to trans-2a.

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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:1998
Deposited On:12 Nov 2013 14:05
Last Modified:07 Dec 2017 23:34
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Swiss Federal Commission for Foreign Students (Bundesstipendiat)
Publisher DOI:https://doi.org/10.1002/hlca.19980810309

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