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Ring transformation of 5-amino (or acylamino)-6-hydroxy (or benzoyloxy)methylpyrimidin-4(3H)-ones into 1H-imidazoles

✍ Scribed by Taisei Ueda; Satoko Asai; Khoji Oiji; Shin-Ichi Nagai; Akito Nagatsu; Jinsaku Sakakibara

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
273 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Treatment of 5‐acylamino‐6‐hydroxy (or benzoyloxy)methyl‐3‐phenylpyrimidin‐4(3__H__)‐one 5,10 with 5% aqueous sodium hydroxide in ethanol gave 2‐alkyl‐5‐hydroxymethyl‐4‐phenylcarbamoyl‐1__H__‐imidazoles 7,11. Oxidation of 5‐amino‐6‐benzoyloxymethyl‐3‐phenylpyrimidin‐4(3__H__)‐one 9 in the presence of copper(II) chloride in alcohol gave 2‐alkoxy‐5‐alkoxymethyl‐4‐phenylcarbamoyl‐1__H__‐imidazoles 12a,b accompanied by 5‐amino‐6‐alkoxymethyl‐3‐phenylpyrimidin‐4(3__H__)‐ones 13a,b.

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