Facile Synthesis of 4,5-Dihydro-1,3,4-Thiadiazoles by 1,3-Dipolar Cycloaddition of Thioisomünchnones

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Contents Vol 62(4)

doi:10.1071/CH08412

Facile Synthesis of 4,5-Dihydro-1,3,4-Thiadiazoles by 1,3-Dipolar Cycloaddition of Thioisomünchnones

Bárbara Sánchez ^A, José Luis Bravo ^A, María José Arévalo ^A, Ignacio López ^B, Mark E. Light ^C, Guadalupe Silvero ^B ^D

^A Departamento de Química Orgánica e Inorgánica, Universidad de Extremadura, Badajoz E-06071, Spain.
^B Departamento de Química Orgánica e Inorgánica, Universidad de Extremadura, Cáceres E-10071, Spain.
^C School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK.
^D Corresponding author. Email: gsilvero@unex.es





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Australian Journal of Chemistry 62(4) 356–359 http://dx.doi.org/10.1071/CH08412
Submitted: 30 September 2008 Accepted: 2 February 2009 Published online: 24 April 2009

Abstract

The present paper summarizes a straightforward synthesis of 4,5-dihydro-1,3,4-thiadiazoles by the 1,3-dipolar cycloaddition of thioisomünchnones. These reactions have been carried out in dichloromethane and are essentially complete within 60 min at room temperature. Under such mild conditions the asymmetric version has been explored as well. Unequivocal structure elucidation has been accomplished by means of one- and two-dimensional NMR techniques as well as X-ray structure analysis.