Fluoroalkylated α,β-Unsaturated Imines as Synthons for the Preparation of Fluorinated Triazinane-2,4-diones and Dihydropyrimidin-2(1H)-ones

Autor:	Ana M. Ochoa de Retana, Francisco Palacios, Guillermo Fernandez de Troconiz, Gloria Rubiales
Rok vydání:	2014
Předmět:	Halogenation Molecular Structure Triazines Organic Chemistry Synthon Regioselectivity Stereoisomerism Pyrimidinones Isocyanate Catalysis chemistry.chemical_compound Tosyl chemistry Organic chemistry Imines Isocyanates
Zdroj:	The Journal of Organic Chemistry. 79:5173-5181
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo500745u
Popis:	A regioselective addition of isocyanates to fluoroalkylated α,β-unsaturated imines 1 is described. Fluoroalkyl-substituted triazinane-2,4-diones 4 are obtained by the reaction of phenyl isocyanate with fluorinated imines 1, while fluorinated dihydropyridin-2(1H)-ones 7 are prepared when tosyl isocyanate is used. Tetrahydro-pyridin-2(1H)-one 10 is obtained by catalytic reduction of dihydropyridin-2(1H)-one 7. Computational studies are performed to explain the different behaviors of both isocyanates and the mechanisms of the processes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e668ede8a290d9b4dad639849bf825cd https://doi.org/10.1021/jo500745u Zobrazit plný text záznamu