Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1H)-ones

Seongil Kang, Subin Park, Kyung-su Kim, Changsik Song and Yunmi Lee*

*Department of Chemistry, Kwangwoon University, Seoul 01897, Republic of Korea, Email: ymleekw.ac.kr

S. Kang, S. Park, K.-s. Kim, C. Song, Y. Lee, J. Org. Chem., 2018, 83, 2694-2705.

DOI: 10.1021/acs.joc.7b03162

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Abstract

A highly efficient Cu-catalyzed aza-Michael addition of 2-aminobenzoates to β-substituted α,β-unsaturated ketones followed by cyclization and a mild oxidation reaction enable a straightforward one-pot synthesis of 3-carbonyl-4-quinolone derivatives in very good yields under mild reaction conditions with short reaction times.

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Key Words

quinolones, oxygen

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ID: J42-Y2018