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4,4-Disubstituierte Imidazol-Derivate aus der Umsetzung von 3-Amino-2H-azirinen mit Salicylamid


Magirius, Florian; Linden, Anthony; Heimgartner, Heinz (1994). 4,4-Disubstituierte Imidazol-Derivate aus der Umsetzung von 3-Amino-2H-azirinen mit Salicylamid. Helvetica Chimica Acta, 77(2):453-462.

Abstract

4,4-Disubstituted Imidazole Derivatives from the Reaction of 3-Amino-2H-azirines with Salicylamide Reaction of 3-amino-2H-azirines 1a-c with salicylamide (7) in MeCN leads to imidazoles 10 and 11 in different rates, depending on the conditions. In the case of 1a and 1b, 11a and 11b, respectively, have been obtained as the main product at 50°; in reactions at 80°, 10a and 10b are the favored products (Tables 1and 2). 2,2-Dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine (1c) reacts with 7 in MeCN mainly to 2-(2-hydroxyphenyl)-5,5-dimethyl-3,5-dihydroimidazol-4-one (10a); in boiling toluene, 11c is formed with low preference (Table 3 ). The structure of the products has been established by spectroscopic means, and in the case of 10b and 11c , by X-ray crystallography. Two different reaction mechanisms for the formation of the products are discussed (Scheme 2).

4,4-Disubstituted Imidazole Derivatives from the Reaction of 3-Amino-2H-azirines with Salicylamide Reaction of 3-amino-2H-azirines 1a-c with salicylamide (7) in MeCN leads to imidazoles 10 and 11 in different rates, depending on the conditions. In the case of 1a and 1b, 11a and 11b, respectively, have been obtained as the main product at 50°; in reactions at 80°, 10a and 10b are the favored products (Tables 1and 2). 2,2-Dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine (1c) reacts with 7 in MeCN mainly to 2-(2-hydroxyphenyl)-5,5-dimethyl-3,5-dihydroimidazol-4-one (10a); in boiling toluene, 11c is formed with low preference (Table 3 ). The structure of the products has been established by spectroscopic means, and in the case of 10b and 11c , by X-ray crystallography. Two different reaction mechanisms for the formation of the products are discussed (Scheme 2).

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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:German
Date:1994
Deposited On:17 Dec 2013 12:15
Last Modified:05 Apr 2016 17:15
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19940770206
Permanent URL: https://doi.org/10.5167/uzh-86619

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