Synthesis of Substituted Pyridine Derivatives via the Ruthenium-Catalyzed Cycloisomerization of 3-Azadienynes

Mohammad Movassaghi* and Matthew D. Hill
Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2006, 128 (14), pp 4592–4593
DOI: 10.1021/ja060626a
Publication Date (Web): March 22, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, movassag@mit.edu

Abstract

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We describe a two-step conversion of various N-vinyl and N-aryl amides to the corresponding substituted pyridines and quinolines, respectively. The process involves the direct conversion of amides, including sensitive N-vinyl amides, to the corresponding trimethylsilyl alkynyl imines followed by a ruthenium-catalyzed protodesilylation and cycloisomerization. A wide range of new alkynyl imines are prepared and readily converted to the corresponding azaheterocycles.

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History

  • Published In Issue April 12, 2006
  • Received January 26, 2006

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