A General Method for the Catalytic Nazarov Cyclization of Heteroaromatic Compounds

John A. Malona, Jessica M. Colbourne, and Alison J. Frontier*
Department of Chemistry, University of Rochester, Rochester, New York, 14627
Org. Lett., 2006, 8 (24), pp 5661–5664
DOI: 10.1021/ol062403v
Publication Date (Web): October 31, 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.

, frontier@chem.rochester.edu

Abstract

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A general, catalytic method for efficient Nazarov cyclization of systems containing heteroaromatic components has been developed. Scandium triflate was identified as the most reactive promoter, and it was found that addition of lithium perchlorate was necessary for synthetically useful catalytic cyclizations. The method was used to synthesize a range of cyclopentanone-fused heteroaromatic systems in 36−97% yield, and the reactivity trends observed demonstrate the impact of polarization on cyclization efficiency.

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History

  • Published In Issue November 23, 2006
  • Received September 29, 2006

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