Reaction of 1,3,5-Triazinanes with Phosphoryl Diazomethanes: Access to 5-Phosphoryl-1,2,3,4-tetrahydropyrimidines
Wenlai Xie, Chengzhuo Wang, Jiaxi Xu
Abstract
Conversion of 1,3,5-triazinanes into 5-phosporyl-1,2,3,4-tetrahydropyrimidines is achieved efficiently through the microwave-assisted reaction with phosphoryl diazomethanes. Both trialkyl and triaryl 1,3,5-triazinanes were converted by diazomethyldiarylphosphine oxides, dialkyl diazomethylphosphonates, and alkyl diazomethyl(aryl)phosphinates and functionalized simultaneously in good to excellent yields. The reaction is a sequence of 1,3,5-triazinane fragmentation, tandem nucleophilic addition of the generated formaldimines and phosphoryl diazomethanes, and final N, N -acetalization.
Topics & Concepts
ChemistryNucleophileAlkylArylMedicinal chemistryTandemFragmentation (computing)Reaction conditionsPhosphoryl chlorideMicrowave irradiationSequence (biology)Combinatorial chemistryOrganic chemistryCatalysisBiochemistryMaterials scienceComputer scienceOperating systemComposite materialSynthesis and Catalytic ReactionsClick Chemistry and ApplicationsChemical Synthesis and Analysis