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

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

Received: 14 June 2006; in revised form: 22 July 2006 / Accepted: 24 July 2006 / Published: 26 July 2006
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: N; N'-Bisarylmethanediamines; dimethylenetriamine; 1; 3; 5-hexahydro-triazines.
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MDPI and ACS Style

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.

AMA Style

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(7):556-563.

Chicago/Turabian Style

Ghandi, Mehdi; Salimi, Farshid; Olyaei, Abolfazl. 2006. "Novel Reaction of N,N'-Bisarylmethanediamines with Formaldehyde. Synthesis of Some New 1,3,5-Triaryl-1,3,5-hexahydrotriazines." Molecules 11, no. 7: 556-563.

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