Organic letters

Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl) anilines

X Zhang, MA Campo, T Yao, RC Larock

Index: Zhang, Xiaoxia; Campo, Marino A.; Yao, Tuanli; Larock, Richard C. Organic Letters, 2005 , vol. 7, # 5 p. 763 - 766

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Citation Number: 168

Abstract

The requisite N-(2-alkynyl)anilines can be easily prepared by the reaction of propargylic mesylates or bromides with anilines. 17 We initially studied the reaction of N-(3-phenyl-2-propynyl)aniline (1) and I 2 . The reaction has been examined with or without various bases such as NaHCO 3 , NaOCO 2 CH 3 , triethylamine, and pyridine and in the presence of different solvents and varying amounts of I 2 . The optimal reaction conditions developed thus far include stirring of 0.30 ...