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Preparation of 1-substituted-5-[(2-oxo-2-phenyl)ethyl]imidazoles

✍ Scribed by Paula Aulaskari; Markku Ahlgrén; Pirjo Vainiotalo; Esko Pohjala

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
478 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

New high yield preparation methods were developed for the pharmaceutically interesting compounds, 1‐benzyl‐, 1‐methyl‐, and 1__H__‐5‐[(2‐oxo‐2‐phenyl)ethyl]imidazoles 1a‐c, respectively. The title compounds were synthesized by four different methods using various starting materials. Two of the methods involved transformation reactions of the key intermediates, 1‐substituted‐5‐[(2‐nitro‐2‐phenyl)ethenyl]imidazoles 2a‐c and 1‐substituted‐5‐[(2‐nitro‐2‐phenyl)ethyl]imidazoles 3a‐c, while the other two utilized the oxidation of 1‐substituted‐5‐[(2‐hydroxy‐2‐phenyl)ethyl]imidazoles 4a‐c, with chromic oxide, and the umpolung reaction of benzaldehyde followed by a condensation reaction of the umpolung intermediate with imidazolecarboxaldehydes 6a‐c.

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