Microwave-Controlled Preparation of Alkenyl-(1H)-1,2,4-triazoles: First Heck Reaction on a (1H)-1,2,4-Triazole Moiety

Ángel Díaz-Ortiz; Pilar Prieto; Abel de Cózar; Cristina Cebrián; Andrés Moreno; Antonio de la Hoz

doi:10.1071/CH09185

RESEARCH ARTICLE

Microwave-Controlled Preparation of Alkenyl-(1H)-1,2,4-triazoles: First Heck Reaction on a (1H)-1,2,4-Triazole Moiety

Ángel Díaz-Ortiz ^A ^B , Pilar Prieto ^A , Abel de Cózar ^A , Cristina Cebrián ^A , Andrés Moreno ^A and Antonio de la Hoz ^A

+ Author Affiliations

- Author Affiliations

^A Dpto. Q. Orgánica, Facultad de Química, Universidad de Castilla-La Mancha, 13071-Ciudad Real, Spain.

^B Corresponding author. Email: Angel.Diaz@uclm.es

Australian Journal of Chemistry 62(12) 1600-1606 https://doi.org/10.1071/CH09185
Submitted: 2 April 2009 Accepted: 12 June 2009 Published: 10 December 2009

Abstract

A new synthetic approach for the preparation of alkenyl-1,2,4-triazole derivatives based on microwave-induced C–C cross-coupling Heck reactions is described. To the best of our knowledge, this is the first application of the Heck reaction to a dihalogenated 1,2,4-triazole. This approach allows the introduction of a wide range of equivalent or different alkenyl substituents in the 5- and/or 3-positions, thus extending the possibilities for the preparation of these valuable derivatives. A similar microwave-induced synthetic procedure has also been applied to the Heck reaction of 4-vinyl-1,2,3-triazoles.

Acknowledgements

Financial support from the DGICYT of Spain through project CTQ2007–60037/BQU and from the Consejería de Educación y Ciencia, JCCM through projects PCI08–0040 and PII2I09–0100–9633 is gratefully acknowledged.

References

Microwave-Controlled Preparation of Alkenyl-(1H)-1,2,4-triazoles: First Heck Reaction on a (1H)-1,2,4-Triazole Moiety

Abstract

Acknowledgements

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