☆ 4.8 Article

Synthesis of 2-Alkenyiquinoline by Reductive Olefination of Quinoline N-Oxide under Metal-Free Conditions

ORGANIC LETTERS (2016)

Journal

ORGANIC LETTERS

Volume 18, Issue 8, Pages 1796-1799

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.6b00522

Keywords

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Categories

Chemistry, Organic

Funding

National Natural Science Foundation of China [21402244]
Foundation for Author of National Excellent Doctoral Dissertation of P. R. China [201425]
Start-up Funding from Sun Yat-Sen University
One Thousand Youth Talents Plan

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Abstract

Synthesis of 2-alkenylquinoline by reductive olefination of quinoline N-oxide under metal-free conditions is disclosed. Practically, the reaction could be performed with quinoline as starting material via a one-pot, two-step process. A possible mechanism is proposed that involves a sequential 1,3-dipolar cycloaddition and acid-assisted ring opening followed by a dehydration process.

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