Oxidative coupling of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone with ethanol and unexpected deacetylative synthesis of 3-hydroxy quinoline

An efficient one pot method for the synthesis of anti-α,β-epoxy ketones from 1-(2-methyl-4-phenylquinolin-3-yl)ethanone and ethanol has been developed by a modified Darzen reaction. The reaction occurs under oxidative conditions via a cascade sequence of bromination, aldol condensation followed by s...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-02, Vol.15 (5), p.1080-1085
Main Authors: Chauhan, Parul, Ravi, Makthala, Kant, Ruchir, Yadav, Prem P
Format: Article
Language:English
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Summary:An efficient one pot method for the synthesis of anti-α,β-epoxy ketones from 1-(2-methyl-4-phenylquinolin-3-yl)ethanone and ethanol has been developed by a modified Darzen reaction. The reaction occurs under oxidative conditions via a cascade sequence of bromination, aldol condensation followed by substitution. The reaction in the presence of NBS and a base however, in the absence of an oxidant, led to the formation of the corresponding 3-hydroxylated product via an unusual rearrangement.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob02336c