Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Reaction of Nitriles under High Pressure. III. The Cyclotrimerization of Aliphatic Nitriles in the Presence of Alcohols and the Rearrangement of the Resulting Trialkyl-1,3,5-triazines to 4-Aminopyrimidines
Koshin YanagiyaMasahiko YasumotoMasahiro Kurabayashi
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1973 Volume 46 Issue 9 Pages 2804-2808

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Abstract

The examination of the simultaneous formation of symmetrically tri-substituted 1,3,5-triazines, 4-amino-2,5,6-substituted pyrimidines and N-pyrimidylamidines in mixtures of lower alcohol and nitrile with more than two hydrogen atoms on the α-position under pressures of a few thousand atm afforded the following information: (1) the triazine is formed by the cyclo-trimerization of the iminoether which is derived from the nitrile and the alcohol; (2) the pyrimidine is formed by the rearrangement of the previously-formed triazine. This rearrangement is caused by an attack of the nucleophilic iminoether on a carbon atom of the triazine ring; and (3) the amidine is assumed to be formed, together with the pyrimidine, by the same attacking mechanism.

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