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Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies

Juan F. Sanz-Cervera*, Raül Blasco, Julio Piera, Michael Cynamon, Ignacio Ibáñez, Marcelo Murguía and Santos Fustero*

*Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46013 Valencia, Spain, Email: juan.f.sanzuv.es, santos.fusterouv.es

J. F. Sanz-Cervera, R. Blasco, J. Piera, M. Cynamon, I. Ibáñez, M. Murguía, S. Fustero, J. Org. Chem., 2009, 74, 8988-8996.

DOI: 10.1021/jo9016265 (free Supporting Information)


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Abstract

A small library of compounds with oxazole and thiazole scaffolds and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson’s reagent to furnish 1,3-thiazoles.

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Key Words

Oxazoles, Thiazoles, Lawesson's reagent


ID: J42-Y2009-3460