Synthesis of N-(4-oxo(thioxo)-1,3,5-triazinan-1-yl)arylamides Using Samarium-Containing Catalysts

Catalytic cycloaminomethylation of ureas and thioureas with N,N-bis(methoxymethyl)alkanamines

“…The use in this reaction of aqueous formaldehyde at elevated temperature reduces the selectivity for triazinan-2-ones [2-4].We have recently synthesized 5-substituted 1,3,5-triazinan-2-ones and 1,3,5-triazinane-2-thiones by catalytic cycloaminomethylation of ureas and thioureas with N,N,N′,N′-tetramethylmetanediamine and primary amines [6], as well as with aromatic carboxylic acid hydrazides [7]. In continuation of our studies in this line, in the present work we examined reactions of urea and its derivatives (thiourea, glycoluril) with N,N-bis(methoxymethyl)alkanamines in the presence of catalysts based on d and f elements with the goal of developing catalytic methods for the selective synthesis of substituted 1,3,5-triazinanes.…”