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Synthesis of Optically Active 1-(1-Phenylethyl)-1H-imidazoles Derived from 1-Phenylethylamine

✍ Scribed by Grzegorz Mlostoń; Paulina Mucha; Katarzyna Urbaniak; Karolina Broda; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
191 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The three‐component reaction of (R)‐ or (S)‐1‐phenylethylamine (6), formaldehyde, and an α‐(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)‐1__H__‐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)‐1__H__‐imidazoles 10 and 2,3‐dihydro‐1‐(1‐phenylethyl)‐1__H__‐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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