NG-Hydroxyguanidines from Primary Amines

Nathaniel I. Martin,* Joshua J. Woodward, and Michael A. Marletta
Department of Chemistry, University of California Berkeley, 204 Lewis Hall, Berkeley, California 94720
Org. Lett., 2006, 8 (18), pp 4035–4038
DOI: 10.1021/ol061454p
Publication Date (Web): July 29, 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.

, nimartin@berkeley.edu

Abstract

Abstract Image

A concise and general method for the preparation of NG-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected NG-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of NG-hydroxy-l-arginine, the intermediate in the enzymatic conversion of l-arginine to nitric oxide and l-citrulline by nitric oxide synthase.

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History

  • Published In Issue August 31, 2006
  • Received June 13, 2006

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