title: Oxidative coupling of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone with ethanol and unexpected deacetylative synthesis of 3-hydroxy quinoline.
abstract: 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.
authors.affiliation: Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow-226031, India. pp_yadav@cdri.res.in ppy_cdri@yahoo.co.in.
authors.forename: Parul
authors.initials: P
authors.lastname: Chauhan
authors.affiliation: Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow-226031, India. pp_yadav@cdri.res.in ppy_cdri@yahoo.co.in.
authors.forename: Makthala
authors.initials: M
authors.lastname: Ravi
authors.affiliation: Division of Molecular and Structural Biology, CSIR-Central Drug Research Institute, Lucknow-226031, India.
authors.forename: Ruchir
authors.initials: R
authors.lastname: Kant
authors.affiliation: Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow-226031, India. pp_yadav@cdri.res.in ppy_cdri@yahoo.co.in.
authors.forename: Prem P
authors.identifier: http://orcid.org/0000-0002-5387-7477
authors.initials: PP
authors.lastname: Yadav