Synlett 2007(3): 0500-0502  
DOI: 10.1055/s-2007-968026
LETTER
© Georg Thieme Verlag Stuttgart · New York

New Ugi/Pictet-Spengler Multicomponent Formation of Polycyclic ­Diketopiperazines from Isocyanides and α-Keto Acids

Laurent El Kaim*, Mathilde Gageat, Laetitia Gaultier, Laurence Grimaud
Laboratoire Chimie et Procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, 75739 Paris Cedex 15, France
Fax: +33(1)45525587; e-Mail: laurent.elkaim@ensta.fr;
Further Information

Publication History

Received 28 July 2006
Publication Date:
07 February 2007 (online)

Zoom Image

Abstract

A new four-component 1,4-diketopiperazine formation is described via an Ugi/Pictet-Spengler two-step procedure. The use of α-ketocarboxylic acids and homoveratryl isocyanide allows the formation of α-keto amides along with cyclised 6-hydroxy­piperazines. The mixtures are not separated but directly treated with trifluoroactic acid to afford a tricyclic 2,5-diketopiperazine in a ­Pictet-Spengler-type cyclisation.