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Concise Synthesis of N-Aryl Tetrahydroquinolines via a One-Pot Sequential Reduction of Quinoline/Chan-Evans-Lam Coupling Reaction

Dipanjan Bhattacharyya, Siddhartha Kumar Senapati, Animesh Das*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati - 781039, Assam, India, Email: adasiitg.ac.in

D. Bhattacharyya, S. K. Senapati, A. Das, Synlett, 2023, 34, 651-656.

DOI: 10.1055/s-0042-1751358


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Abstract

Boronic acid catalyzed one-pot reductions of quinolines with Hantzsch ester followed by N-arylations via external base-free Chan-Evans-Lam coupling provide N-aryl tetrahydroquinolines under mild reaction conditions. The use of an inexpensive N-arylation protocol, aerobic reaction conditions, and functional group diversity are important practical features.

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Key Words

tetrahydroquinolines, Chan-Lam coupling, one-pot reaction, Hantzsch ester


ID: J72-Y2023