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Synfacts 2006(10): 1003-1003
DOI: 10.1055/s-2006-949351
DOI: 10.1055/s-2006-949351
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Cyclic Dipeptidyl Ureas via Ugi Three-Component Reaction
M. Sañudo, S. Marcaccini*, S. Basurto, T. Torroba
Universidad de Burgos, Spain and Università di Firenze, Sesto Fiorentino, Italy
Further Information
Publication History
Publication Date:
21 September 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200610/lookinside/thumbnails/10.1055-s-2006-949351-1.jpg)
Significance
For the first time, semicarbazones are employed in the Ugi three-component reaction with isocyanates and α-keto acids to give 1,1-disubstituted semicarbazides. The products conveniently precipitate from solution under these reaction conditions. An X-ray crystal structure analysis was obtained of one adduct. Treatment with sodium ethoxide followed by methylation using diazomethane affords [1,2,4]-triazine derivatives. The sequence appears to be of general value for the synthesis of such 6-oxo[1,2,4]triazin-1-yl derivatives.