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Regioselective Synthesis of C-3-Functionalized Quinolines via Hetero-Diels-Alder Cycloaddition of Azadienes with Terminal Alkynes

Rakesh K. Saunthwal, Monika Patel and Akhilesh K. Verma*

*Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India, Email: avermaacbr.du.ac.in

R. K. Saunthwal, M. Patel, A. K. Verma, J. Org. Chem., 2016, 81, 6563-6572.

DOI: 10.1021/acs.joc.6b01186 (free Supporting Information)


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Abstract

[4 + 2] Cycloaddition of azadienes (in situ generated from 2-aminobenzyl alcohol) and terminal alkynes enables a highly efficient metal and protection-free approach for the regioselective synthesis of C-3-functionalized quinolines, which are difficult to access.

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Hetero-Diels-Alder Cycloaddition of Azadienes with Terminal Alkynes



Key Words

Quinolines, Diels-Alder Reaction


ID: J42-Y2016