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Synthesis of optically active 1-(1-phenylethyl)imidazoles eerived from 1-phenylethylamine


Mloston, G; Mucha, P; Urbaniak, K; Broda, K; Heimgartner, H (2008). Synthesis of optically active 1-(1-phenylethyl)imidazoles eerived from 1-phenylethylamine. Helvetica Chimica Acta, 91(2):232-238.

Abstract

The three-component reaction of (R)- or (S)-1-phenylethylamine (6), formaldehyde, and an -(hydroxyimino) ketone 5, i.e., 3-(hydroxyimino)butan-2-one (5a) or 2-(hydroxyimino)-1,2-diphenylethanone (5b), yields the corresponding enantiomerically pure 1-(1-phenylethyl)-1H-imidazole 3-oxide 7 in high yield (Schemes 2 and 3). The reactions are carried out either in MeOH or in AcOH. Smooth transformations of the N-oxides into optically active 1-(1-phenylethyl)-1H-imidazoles 10 and 2,3-dihydro-1-(1-phenylethyl)-1H-imidazole-2-thiones 11 are achieved by treatment of 7 with Raney-Ni and 2,2,4,4-tetramethyl-3-thioxocyclobutanone (12), respectively (Scheme 4).

Abstract

The three-component reaction of (R)- or (S)-1-phenylethylamine (6), formaldehyde, and an -(hydroxyimino) ketone 5, i.e., 3-(hydroxyimino)butan-2-one (5a) or 2-(hydroxyimino)-1,2-diphenylethanone (5b), yields the corresponding enantiomerically pure 1-(1-phenylethyl)-1H-imidazole 3-oxide 7 in high yield (Schemes 2 and 3). The reactions are carried out either in MeOH or in AcOH. Smooth transformations of the N-oxides into optically active 1-(1-phenylethyl)-1H-imidazoles 10 and 2,3-dihydro-1-(1-phenylethyl)-1H-imidazole-2-thiones 11 are achieved by treatment of 7 with Raney-Ni and 2,2,4,4-tetramethyl-3-thioxocyclobutanone (12), respectively (Scheme 4).

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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 12:04
Last Modified:05 Apr 2016 12:57
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.200890028

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