Synthesis of variously 9,9-dialkylated octahydropyrimido [3,4- a]- s-triazines with potential antifungal activity

Abstract

9,9-Dialkyloctahydropyrimido[3,4- a]- s-triazines were synthesized by iminodimethylation reaction between a 5,5-dialkyl-6-aminopyrimidine-2,4(3 H,5 H)-dione, a substituted aniline and two moles of formaldehyde. The synthesis of 5,5-dialkyl-6-aminopyrimidinedione consisted of the condensation of urea with ethyl 2,2-dialkylcyanoacetates. 18 Octahydropyrimido[3,4- a]- s-triazines were synthesized and compounds resulting from a supplementary aminomethylation were also obtained. Most of these compounds were tested for antifungal activity in vitro. Only 9,9-dibutyl-6,8-dioxo-3(2-chlorophenyl)2,3,4,5,6,7,8,9-octahydropyrimido[3,4- a]- s-triazine showed some activity against Microsporum canis.