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Addition of carboxylic acidis and cyclic 1,3-diketones to 2-dimethylamino-3,3-dimethyl-1-azirine


Vittorelli, Piero; Heimgartner, Heinz; Schmid, Hans; Hoet, P; Ghosez, Leon (1974). Addition of carboxylic acidis and cyclic 1,3-diketones to 2-dimethylamino-3,3-dimethyl-1-azirine. Tetrahedron, 30:3737-3740.

Abstract

The reaction of 2-dimethylamino-3,3-dimethyl-1-azirine 1 with carboxylic acids 2a-e at room temperature in inert solvents generates rearranged 1:1 adducts in 65-92% yields. These adducts are N-acyl derivatives of 2-amino-N,N-dimethyl-isobutyramide 3a-e resulting from 1,2 addition of the acid followed by 1,2 ring cleavage and transfer of an acyl group. Cyclic enolizable 1,3 diketones 4a-c react similarly with 1 to yield the corresponding rearranged 1:1 adducts 5a-c, whereas acyclic diketones or ethyl acetoacetate are inert under comparable experimental conditions.

The reaction of 2-dimethylamino-3,3-dimethyl-1-azirine 1 with carboxylic acids 2a-e at room temperature in inert solvents generates rearranged 1:1 adducts in 65-92% yields. These adducts are N-acyl derivatives of 2-amino-N,N-dimethyl-isobutyramide 3a-e resulting from 1,2 addition of the acid followed by 1,2 ring cleavage and transfer of an acyl group. Cyclic enolizable 1,3 diketones 4a-c react similarly with 1 to yield the corresponding rearranged 1:1 adducts 5a-c, whereas acyclic diketones or ethyl acetoacetate are inert under comparable experimental conditions.

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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:1974
Deposited On:01 Dec 2014 16:08
Last Modified:05 Apr 2016 18:33
Publisher:Elsevier
ISSN:0040-4020
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, Institut pour l'Encouragement de la Recherche Scientifique dans l'Industrie et l'Agriculture, Fonds der la Recherche Fondamentale Collective (Belgium)
Publisher DOI:https://doi.org/10.1016/S0040-4020(01)90659-3
Permanent URL: https://doi.org/10.5167/uzh-101481

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