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Synthesis of Polysubstituted Quinolines via Transition-Metal-Free Oxidative Cycloisomerization of o-Cinnamylanilines

Mohammad Rehan, Gurupada Hazra and Prasanta Ghorai*

*Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhouri, Bhopal-462066, India, Email: pghoraiiiserb.ac.in

M. Rehan, G. Hazra, P. Ghorai, Org. Lett., 2015, 17, 1668-1671.

DOI: 10.1021/acs.orglett.5b00419 (free Supporting Information)


Abstract

A regioselective 6-endo-trig intramolecular oxidative cyclization enabled an efficient synthesis of 2-aryl 4-substituted quinolines from stable and readily available o-cinnamylanilines with KOtBu as a mediator and DMSO as an oxidant at rt. The reaction showed a broad substrate scope with very good yields.

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Key Words

quinolines, DMSO


ID: J54-Y2015