Reactions with 2,4-Dioxohexahydro-1,3,5-triazin

Article abstract of DOI:10.1007/BF00806856

2,4-Dioxohexahydro-1,3,5-triazin (DHT) reacts with formaldehyde and secondary amines (Mannich reaction) to the corresponding 1,3,5- or 1,5-aminomethyl-DHTs (1a-8a or 1b-11b). DHT and formaldehyde give the methylol compounds 12a, 12b, and 12c. Alkylation of DHT with alkyl halides in presence of base and dimethyl-sulfoxide as the solvent affords the tri-N-alkyl derivatives 14-22. 1,5-Dimorpholinomethyl-DHT (1b) can be alkylated in position 3 with alkyl halides. The morpholinomethyl groups in positions 1 and 5 behave as protecting groups and are easily removable. Thus, it is possible to introduce different alkyl substituents into the molecule. The reaction of 1b with dihaloalkanes results in a coupling of two DHT molecules via the nitrogen in position 3 (compounds 26-29).