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Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.

ABSTRACT: A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I(2), Br(2), PhSeBr and p-O(2)NC(6)H(4)SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)(2)-catalyzed ring closure of these same alkynylanilines.

SUBMITTER: Zhang X 

PROVIDER: S-EPMC2813516 | biostudies-other | 2010 Feb

REPOSITORIES: biostudies-other

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Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.

Zhang Xiaoxia X   Yao Tuanli T   Campo Marino A MA   Larock Richard C RC  

Tetrahedron 20100201 6

A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I(2), Br(2), PhSeBr and p-O(2)NC(6)H(4)SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)(2)-catalyzed ring closure of these same  ...[more]

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