An efficient, one-pot synthetic protocol toward triazinane diones, a rather unexplored class of heterocyclic scaffolds combining phosphonates, nitriles, aldehydes, and isocyanates is described. The optimization of the reaction, synthesis of a small library of different triazinane diones, as well as alternative routes toward the triazinane dione scaffold are discussed.
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Org Lett
March 2024
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China.
This study demonstrates a highly efficient regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence of a diphosphine ligand, the reaction proceeds via a (5+2) cycloaddition pathway to afford 1,3-diazepin-4-ones in excellent yields, while using a monophosphine ligand, the reaction proceeds smoothly via a (3+2) cycloaddition pathway to give imidazolidin-4-ones in good yields.
View Article and Find Full Text PDFJ Org Chem
June 2014
Departamento de Química Orgánica I and Centro de Investigacion Lascaray (Lascaray Research Center) Facultad de Farmacia, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU) , Paseo de la Universidad 7, 01006 Vitoria, Spain.
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.
View Article and Find Full Text PDFOrg Biomol Chem
September 2008
Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081, HV, Amsterdam, The Netherlands.
Triazinane diones, readily generated by a recently reported multicomponent reaction, can be easily alkylated with various alkyl halides, allowing a wide variety of complexity-generating secondary reactions. Because of the high variability of the initial multicomponent reactions and the multiple possibilities for participation of substituents in the secondary reactions, a highly diverse set of complex products was obtained in short and efficient reaction sequences.
View Article and Find Full Text PDFJ Org Chem
January 2008
Department of Chemistry & Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV, Amsterdam, The Netherlands
An efficient, one-pot synthetic protocol toward triazinane diones, a rather unexplored class of heterocyclic scaffolds combining phosphonates, nitriles, aldehydes, and isocyanates is described. The optimization of the reaction, synthesis of a small library of different triazinane diones, as well as alternative routes toward the triazinane dione scaffold are discussed.
View Article and Find Full Text PDFActa Crystallogr C
July 2000
Department of Chemistry, Technion-Israel Institute of Technology, Haifa, Israel.
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