Novel reaction of N,N'-bisarylmethanediamines with formaldehyde. Synthesis of some new 1,3,5-triaryl-1,3,5-hexahydrotriazines.
The acid-catalyzed cyclocondensation of N,N'-bisaryl (aryl = 2-pyrimidinyl, 2-pyrazinyl and 4-nitrophenyl) methanediamines 5a-c with aqueous formaldehyde in refluxing acetonitrile leads to the formation of the corresponding 1,3,5-triaryl-1,3,5-hexa-hydrotriazines 6a-c. The stoichiometric reactions of 2-aminopyrimidine and 2-amino-pyrazine with aqueous formaldehyde in acetonitrile under reflux conditions also afforded 6a and 6b, respectively. Treatment of 2-aminopyrimidine with aqueous formaldehyde in a 3:2 ratio yielded N,N',N"-tris(2-pyrimidinyl)dimethylenetriamine (7a) as a sole product, which upon subsequent reaction with formaldehyde also afforded 6a. The reaction of N,N'-biphenylmethanediamine with formaldehyde was also investigated.
Ghandi
Mehdi
M
School of Chemistry, University College of Science, University of Tehran, Tehran, Iran. ghandi@khayam.ut.ac.ir
Salimi
Farshid
F
Olyaei
Abolfazl
A
D002384:Catalysis; D003959:Diamines / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry*; D005561:Formates / Q000737:chemistry; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry
D003959:Diamines; D005561:Formates; D014227:Triazines; C030544:formic acid; D005557:Formaldehyde