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Synthesis and selected transformations of 1H-imidazole 3-oxides derived from amino acid esters


Jasinski, M; Mloston, G; Linden, A; Heimgartner, H (2008). Synthesis and selected transformations of 1H-imidazole 3-oxides derived from amino acid esters. Helvetica Chimica Acta, 91(10):1916-1933.

Abstract

A series of new optically active 1H-imidazole 3-oxides 5 with a substituted acetate group at N(1) as the chiral unit were prepared by the reaction of a-(hydroxyimino) ketones, a-amino acid methyl esters, and formaldehyde. In an analogous reaction, ethyl 2-(hydroxyimino)-3-oxobutyrate and 1,3,5- trialkylhexahydro-1,3,5-triazines gave 3-oxido-1H-imidazole-4-carboxylates 14, which easily rearranged into the 2-oxo derivatives 15. Selected examples of N-oxides 5 could be transformed into the corresponding 2,3-dihydro-1H-imidazole-2-thione derivatives 10 via a 'sulfur-transfer reaction', and the reduction of the histidine derivative 5i with Raney-Ni yielded the optically active 2,3-bis(imidazolyl)propanoate 12.
Furthermore, reaction of the (1H-imidazol-1-yl)acetates with primary amines yielded the corresponding acetamides.

Abstract

A series of new optically active 1H-imidazole 3-oxides 5 with a substituted acetate group at N(1) as the chiral unit were prepared by the reaction of a-(hydroxyimino) ketones, a-amino acid methyl esters, and formaldehyde. In an analogous reaction, ethyl 2-(hydroxyimino)-3-oxobutyrate and 1,3,5- trialkylhexahydro-1,3,5-triazines gave 3-oxido-1H-imidazole-4-carboxylates 14, which easily rearranged into the 2-oxo derivatives 15. Selected examples of N-oxides 5 could be transformed into the corresponding 2,3-dihydro-1H-imidazole-2-thione derivatives 10 via a 'sulfur-transfer reaction', and the reduction of the histidine derivative 5i with Raney-Ni yielded the optically active 2,3-bis(imidazolyl)propanoate 12.
Furthermore, reaction of the (1H-imidazol-1-yl)acetates with primary amines yielded the corresponding acetamides.

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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:2008
Deposited On:06 Feb 2009 10:10
Last Modified:05 Apr 2016 12:57
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Polish Ministry of Science and Higher Education, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200890205

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