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Metal-Free Synthesis of 2-Substituted Quinolines via High Chemoselective Domino Condensation/Aza-Prins Cyclization/Retro-Aldol between 2-Alkenylanilines with β-Ketoesters

Jiang Nan*, Pu Chen, Yuxin Zhang, Yun Yin, Bo Wang and Yangmin Ma*

*College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China, Email: nanjiangsust.edu.cn, mym63sina.com

J. Nan, P. Chen, Y. Zhang, Y. Yin, B. Wang, Y. Ma, J. Org. Chem., 2020, 85, 14042-14054.

DOI: 10.1021/acs.joc.0c02063 (free Supporting Information)


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Abstract

A highly chemoselective domino condensation/aza-Prins cyclization/retro-aldol between 2-alkenylanilines and β-dicarbonyl compounds provides a large variety of valuable 2-substituted quinolines in good yields. This metal-free reaction tolerates a broad range of functional groups and can even be simpliefied into a three component domino reaction.

 
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Key Words

quinolines


ID: J42-Y2020