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Synfacts 2010(2): 0152-0152
DOI: 10.1055/s-0029-1219116
DOI: 10.1055/s-0029-1219116
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 6-Fluorinated 3,4-Dihydro-pyrimidinones
S. Fustero*, S. Catalán, J. L. Aceña, C. del Pozo
Universidad de Valencia, Burjassot and Centro de Investigación Príncipe Felipe, Valencia, Spain
Further Information
Publication History
Publication Date:
21 January 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201002/lookinside/thumbnails/10.1055-s-0029-1219116-1.jpg)
Significance
Reported is the reaction of ethyl 3-butenoate 1 with fluorinated cyanides 2 to form products 3 which upon condensation with iso(thio)cyanates 5 lead to fluorinated 3,4-dihydropyrimidinones 6 via a terminal intramolecular aza-Michael reaction. The formation of the thermodynamic products 3 was achieved by slow addition of the fluorinated cyanides 2 to the lithium enolate of 1 (fast addition leads to the kinetic products 4). The yields of 3 are modest due to their instability during purification. The 6-fluorinated pyrimidinones 6 were thus obtained in low to moderate yields, with better yields being achieved in case of isothiocyanates.