Synlett 2016; 27(12): 1873-1877
DOI: 10.1055/s-0035-1561976
letter
© Georg Thieme Verlag Stuttgart · New York

A Simple Entry to Yne-amides from Yne-oxazolidinones

Charles S. Demmer, Gwilherm Evano*
  • Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: gevano@ulb.ac.be
Further Information

Publication History

Received: 11 February 2016

Accepted after revision: 10 March 2016

Publication Date:
05 April 2016 (eFirst)

Abstract

A convenient entry to yne-amides, useful building blocks for chemical synthesis whose synthesis can be rather difficult – especially in the acyclic series – is reported. They were found to be readily obtained by a simple ring opening of the corresponding, readily available yne-oxazolidinones with organolithium reagents. Surprisingly, no competitive carbolithiation of the highly reactive nitrogen-substituted alkyne or propargylic lithiation were observed, this method therefore providing a useful entry to yne-amides which can be obtained in fair to good yields.

Supporting Information