A method for the synthesis of substituted quinolines via electrophilic cyclization of 1-azido-2-(2-propynyl)benzene

Zhibao Huo, Ilya D. Gridnev, Yoshinori Yamamoto

Research output: Contribution to journalArticle

126 Citations (Scopus)

Abstract

(Chemical Equation Presented) A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br 2 , ICl, NBS, NIS, and HNTf2) in CH3NO 2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, orH, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst.

Original languageEnglish
Pages (from-to)1266-1270
Number of pages5
JournalJournal of Organic Chemistry
Volume75
Issue number4
DOIs
Publication statusPublished - 2010 Feb 19

ASJC Scopus subject areas

  • Organic Chemistry

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