Regioselective Synthesis of Substituted Pyrroles:  Efficient Palladium-Catalyzed Cyclization of Internal Alkynes and 2-Amino-3-iodoacrylate Derivatives

Matthew L. Crawley,*† Igor Goljer,‡ Douglas J. Jenkins,† John F. Mehlmann,† Lisa Nogle,‡ Rebecca Dooley,‡ and Paige E. Mahaney†
Discovery Medicinal Chemistry and Discovery Analytical Chemistry, Wyeth Research, 500 Arcola Road, Collegeville, Pennsylvania 19426
Org. Lett., 2006, 8 (25), pp 5837–5840
DOI: 10.1021/ol062424p
Publication Date (Web): November 10, 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.

,
†

 Discovery Medicinal Chemistry.

,
‡

 Discovery Analytical Chemistry.

, crawlem@wyeth.com

Abstract

Abstract Image

The first efficient and regioselective palladium-catalyzed cyclization of internal alkynes and 2-amino-3-iodoacrylates to give moderate to excellent yields of highly functionalized pyrroles has been developed. This approach is applicable to a range of alkynes and affords the deacylated pyrrole under reaction conditions for most substrates.

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History

  • Published In Issue December 07, 2006
  • Received October 2, 2006

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