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Preparation of 2,4,5-triarylimidazol-4-ols and their stereoselective rearrangement by 1,5-phenyl migration

✍ Scribed by Gonghao Lu; Akira Katoh; Zhiqiang Zhang; Zhizhi Hu; Peng Lei; Masaru Kimura

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
720 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Lophine hydroperoxides underwent base‐triggered 1,5‐phenyl migration in DMSO to afford imidazolones in high yields, instead of amidines with chemiluminescence (CL). The corresponding imidazolols were believed to intermediates and they were successfully obtained by treating the peroxides with DMSO without the base. The diminished CL was because of the reduction of the hydroperoxides with DMSO. The imidazolols subsequently underwent smooth base‐mediated rearrangement to afford imidazolones. Furthermore, the chiral imidazolols provided stereoselective imidazolones in high enantiomeric excess (>92%), which supported the mechanism of an intramolecular ring for the migration. J. Heterocyclic Chem., (2010).

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