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Paper | Regular issue | Vol 29, No. 3, 1989, pp.539-545
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4846
A Facile Synthesis of 2-Aryl- and 2-Heteroaryl-substituted 4-Aminoquinolines

Lucjan Strekowski,* Suk-Bin Kong, Marek T. Cegla, and Donald B. Harden

*Department of Chemistry, Georgia State University, University Plaza, Atlanta, GA 30303, U.S.A.


Schiff’s bases, obtained from 2-aminobenzonitrile and aryl or heteroaryl methyl ketones, are lithiated with lithium diisopropylamide at the methyl group. The intermediate carbanions undergo cyciization to a quinoline system in a high yield. The corresponding Schiff’s base obtained from propiophenone undergoes an unusual addition reaction with the lithium reagent instead.