4.7 Article

[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 5, Pages 2797-2808

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02708

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A method for the synthesis of pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (=CH-) synthon is disclosed. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields.
A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (=CH-) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (=CH-) to the pyridine ring in quinoline molecules. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields. On the basis of the control experiments and the literature, a plausible mechanism is proposed.

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