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1,3-Dipolar Cycloadditions with 1-Alkoxy-substituted Nitrile Ylides


Bojkova, Nina; Heimgartner, Heinz (1998). 1,3-Dipolar Cycloadditions with 1-Alkoxy-substituted Nitrile Ylides. Heterocycles, 47(2):781-792.

Abstract

Thermolysis of 4-alkoxy-l,3-oxazol-5(2H)-ones (2) (X = O) leads to reactive nitrile ylides (1) bearing an alkoxy substituent at the nitrile C-atom. These intermediates can be trapped by C,C-, C,O-, C,N-, and C,S-dipolarophiles, yielding 5-membered heterocycles via 1,3- dipolar cycloaddition. In the case of 1,3-thiazole-5(4H)-thiones (11) as dipolarophiles, two regioisomeric cycloadducts were obtained. The results of the cycloadditions are discussed with respect to the influence of the alkoxy substituent on the structure of the nitrile ylide.

Abstract

Thermolysis of 4-alkoxy-l,3-oxazol-5(2H)-ones (2) (X = O) leads to reactive nitrile ylides (1) bearing an alkoxy substituent at the nitrile C-atom. These intermediates can be trapped by C,C-, C,O-, C,N-, and C,S-dipolarophiles, yielding 5-membered heterocycles via 1,3- dipolar cycloaddition. In the case of 1,3-thiazole-5(4H)-thiones (11) as dipolarophiles, two regioisomeric cycloadducts were obtained. The results of the cycloadditions are discussed with respect to the influence of the alkoxy substituent on the structure of the nitrile ylide.

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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 13:52
Last Modified:07 Dec 2017 23:34
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Professor Hans. E. Schmid-Stiftung
Publisher DOI:https://doi.org/10.3987/COM-97-S(N)74

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