Russian journal of organic chemistry

Quinonimine Formation in the Reaction of 6-Hydroxy-2, 2, 4-trimethyl-1, 2-dihydroquinoline with 1-Chloro-2, 3-epoxypropane

ZV Shmyreva, LF Ponomareva

Index: Shmyreva; Ponomareva Russian Journal of Organic Chemistry, 2002 , vol. 38, # 3 p. 456 - 456

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Abstract

We have revealed an anomalous reaction of 6-hydroxy-2, 2, 4-trimethyl-1, 2- dihydroquinoline (I) with 1-chloro-2, 3-epoxypropane (II). Instead of expected O-alkylation, which is typical of reactions of II with phenols [1], oxidation of quinoline I occurred to give 2, 2, 4-trimethyl-2, 6-dihydroquinolin-6-one (III):