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The Reaction of 3-(Dimethylamino)-2H-azirines with 2,3-Pyridinedicarboximide


Obrecht, Jean-Pierre; Schönholzer, Peter; Jenny, Christian Johannes; Prewo, Roland; Heimgartner, Heinz (1988). The Reaction of 3-(Dimethylamino)-2H-azirines with 2,3-Pyridinedicarboximide. Helvetica Chimica Acta, 71(5):1319-1327.

Abstract

Reaction of 2,2-dialkyl-3-(dimethylamino)-2H-azirines 1a and 1b with 2,3-pyridinedicarboximide (4) in MeCN or DMF at room temperature yielded two regioisomeric tricyclic 1:1 adducts, the azacyclols 11/12 and 16/17,respectively (Schemes 3 and 4). The structure of 12 was established by X-ray crystallography. Methanolysis of 11/12 and 16/17 led to mixtures of methyl [4,4-dialkyl-5-(dimethylamino)-4H-imidazol-2-yl]pyridine carboxylates 13/14 and 18/19, respectively. The structure of compound 14 is closely related to that of the powerful herbicide 9 (Scheme 9), i.e. the described reactions offer a new synthetic approach to this class of compounds. A mechanistic interpretation for the formation of regioisomeric 1:1 adducts as well as methyl (imidazol-2-y1)pyridine carboxylates is depicted in Scheme 5.

Abstract

Reaction of 2,2-dialkyl-3-(dimethylamino)-2H-azirines 1a and 1b with 2,3-pyridinedicarboximide (4) in MeCN or DMF at room temperature yielded two regioisomeric tricyclic 1:1 adducts, the azacyclols 11/12 and 16/17,respectively (Schemes 3 and 4). The structure of 12 was established by X-ray crystallography. Methanolysis of 11/12 and 16/17 led to mixtures of methyl [4,4-dialkyl-5-(dimethylamino)-4H-imidazol-2-yl]pyridine carboxylates 13/14 and 18/19, respectively. The structure of compound 14 is closely related to that of the powerful herbicide 9 (Scheme 9), i.e. the described reactions offer a new synthetic approach to this class of compounds. A mechanistic interpretation for the formation of regioisomeric 1:1 adducts as well as methyl (imidazol-2-y1)pyridine carboxylates is depicted in Scheme 5.

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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:1988
Deposited On:14 May 2014 08:59
Last Modified:08 Dec 2017 05:24
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation
Publisher DOI:https://doi.org/10.1002/hlca.19880710542

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