MANNICH REACTION OF 1-N-BUTYL-3-P-TOSYLUREA .1. SYNTHESES OF BUTYL-2-OXO-1,5-DI-P-TOSYL-PERHYDRO-1,3,5-TRIAZINE AND DI-N-BUTYL-2-OXO-1-P-TOSYL-PERHYDRO-1,3,5-TRIAZINE
Gc. Ebi et al., MANNICH REACTION OF 1-N-BUTYL-3-P-TOSYLUREA .1. SYNTHESES OF BUTYL-2-OXO-1,5-DI-P-TOSYL-PERHYDRO-1,3,5-TRIAZINE AND DI-N-BUTYL-2-OXO-1-P-TOSYL-PERHYDRO-1,3,5-TRIAZINE, Chemical and Pharmaceutical Bulletin, 44(4), 1996, pp. 639-641
1-n-Butyl-3-p-tosylurea (tolbutamide) does not incorporate the seconda
ry amines, piperidine, diethylamine, dimethylamine, dipropylamine, pyr
rolidine and morpholine, to any significant extent in its normal Manni
ch reaction under alkaline conditions in refluxing methanol, accetonit
rile and dioxane, Instead -butyl-2-oxo-1,5-di-p-tosylperhydro-1,3,5-tr
iazine and di-n-butyl-2-oxo-1-p-tosyl-perhydro-1,3,5-triazine are main
ly formed usually in good yields, These triazines have been isolated a
nd characterized, and a mechanism is proposed for their formation.