Synthesis 2014; 46(18): 2451-2462
DOI: 10.1055/s-0033-1339139
paper
© Georg Thieme Verlag Stuttgart · New York

Oxazole/Thiazole and Triazole Hybrids Based on α-Amino Acids

Guillermo Valdomir
a  Cátedra de Química Farmacéutica, DQO, Facultad de Química, UdelaR, Av General Flores 2124, 11800 Montevideo, Uruguay   Fax: +598(2)9241906   Email: [email protected]
,
Juan I. Padrón
b  Instituto de Productos Naturales y Agrobiología, CSIC, C/ Astrofísico Francisco Sánchez 3, 38206 La Laguna, Spain
c  Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Sánchez 2, 38206 La Laguna, Spain
,
José M. Padrón
c  Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Sánchez 2, 38206 La Laguna, Spain
,
Víctor S. Martín
c  Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Sánchez 2, 38206 La Laguna, Spain
,
Danilo Davyt*
a  Cátedra de Química Farmacéutica, DQO, Facultad de Química, UdelaR, Av General Flores 2124, 11800 Montevideo, Uruguay   Fax: +598(2)9241906   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 30 January 2014

Accepted after revision: 29 April 2014

Publication Date:
04 June 2014 (online)


Abstract

The Cu(I)-catalyzed Huisgen [3+2] cycloaddition is the basis of click chemistry to synthesize triazole derivatives by coupling azides with ethynyl blocks. In the development of new compounds inspired by bioactive natural products, the synthesis of new oxazole building blocks containing azide moiety and coupling them with aromatic alkynes via triazole linker is described. These oxazole building blocks are synthesized using amino acids as chiral and inexpensive starting materials. Using this approach, 16 new triazole-oxazole hybrids were synthesized.

Supporting Information

 
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