Zum Reaktionsverhalten von 2,4-Dioxohexahydro-1,3,5-triazin

Summary 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 or1b–11b).DHT and formaldehyde give the methylol compounds12a,12b, and12c. Alkylation ofDHT with alkyl halides in presence of base and dimethyl-sulfoxide as the solvent affords the tri-N-alkyl derivatives14–22. 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 of1b with dihaloalkanes results in a coupling of twoDHT moleculesvia the nitrogen in position 3 (compounds26–29).

Herrn Professor Dr. mult.Friedrich Asinger zum 90. Geburtstag gewidmet