Synthesis 2007(7): 1115-1119  
DOI: 10.1055/s-2007-965940
PSP
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Substituted Pyridines and Quinolines

Matthew D. Hill, Mohammad Movassaghi*
Department of Chemistry, Massachusettes Institute of Technology, Cambridge, MA 02139, USA
Fax: +1(617)2521504; e-Mail: movassag@mit.edu;
Further Information

Publication History

Received 23 November 2006
Publication Date:
20 February 2007 (online)

Abstract

A variety of N-vinyl and N-aryl amides were converted to the corresponding pyridine and quinoline derivatives, respectively. Amide activation and nucleophilic addition of copper(I) (trimethylsilyl)acetylide efficiently provided the desired alkynyl imines. Ruthenium­-catalyzed protodesilylation and cycloisomerization of these imines gave the corresponding azaheterocycles.