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Molecules 2006, 11(7), 556-563; doi:10.3390/11070556

Novel Reaction of N,N'-Bisarylmethanediamines with Formaldehyde. Synthesis of Some New 1,3,5-Triaryl-1,3,5-hexahydrotriazines

School of Chemistry, University College of Science, University of Tehran, Tehran, Iran
Author to whom correspondence should be addressed.
Received: 14 June 2006 / Revised: 22 July 2006 / Accepted: 24 July 2006 / Published: 26 July 2006
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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. View Full-Text
Keywords: N; N'-Bisarylmethanediamines; dimethylenetriamine; 1; 3; 5-hexahydro-triazines. N; N'-Bisarylmethanediamines; dimethylenetriamine; 1; 3; 5-hexahydro-triazines.

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Ghandi, M.; Salimi, F.; Olyaei, A. Novel Reaction of N,N'-Bisarylmethanediamines with Formaldehyde. Synthesis of Some New 1,3,5-Triaryl-1,3,5-hexahydrotriazines. Molecules 2006, 11, 556-563.

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