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On the methylation of 3-cyano-6-hydroxypyridine-2(1H)-ones

✍ Scribed by Yves Louis Janin; Jaouad Chiki; Michel Legraverend; Christiane Huel; Emile Bisagni

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
459 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

In order to prepare new heterocyclic derivatives as building block for compounds with potential biological activities, we were led to study the O-methylation of 3-cyano-6-hydroxypyridine-2(IH)-ones such as 1. This enabled us to develop a new two steps method to prepare the corresponding 2,6-dimethoxy derivative 5 in 80 % yield. It consisted first in heating 1 in trimethylorthoformate, with or without an acidic catalyst, which gave a mixture of the two mono-methoxy isomers, then a classical methylation of the secood hydroxy moiety led almost exclusively to 5. In this paper we present this "methylation" method and various unexpected results recorded when we attempted to extend it to related derivatives or to other heterocycle containing lactim-lactam functions. An intramolecular transetherification mechanism requiring the simultaneous transfer of a hydrogen and a methyl is suggested.

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