Oxidative coupling of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone with ethanol and unexpected deacetylative synthesis of 3-hydroxy quinolineElectronic supplementary information (ESI) available: Experimental procedures, compound characterization, X-ray crystal structure data and ORTEP drawing for 2a; copies of NMR spectra of all the final compounds. CCDC 1492781. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6ob02336c

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. An efficient, one pot method for the synthesis of α,β-epoxy ketone and hydroxylation has been developed from 1-(2-methyl-4-phenylquinolin-3-yl)ethanone with alcohol under mild conditions.