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

Full Text: HTML

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 ...

Synthesis of 7H-indolo [2, 3-c] quinolines: study of the Pd-catalyzed intramolecular arylation of 3-(2-bromophenylamino) quinolines under microwave irradiation

[Hostyn, Steven; Maes, Bert U.W.; Van Baelen, Gitte; Gulevskaya, Anna; Meyers, Caroline; Smits, Koen Tetrahedron, 2006 , vol. 62, # 19 p. 4676 - 4684]

Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine

[Hostyn, Steven; Maes, Bert U.W.; Pieters, Luc; Lemiere, Guy L.F.; Matyus, Peter; Hajos, Gyoergy; Dommisse, Roger A. Tetrahedron, 2005 , vol. 61, # 6 p. 1571 - 1577]

… of Quinolines, 2-Quinolones, Phenanthridines, and 6 (5 H)-Phenanthridinones via Palladium [0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β- …

[Banwell, Martin G.; Lupton, David W.; Ma, Xinghua; Renner, Jens; Sydnes, Magne O. Organic Letters, 2004 , vol. 6, # 16 p. 2741 - 2744]