J. Streef, H. J. Hertog
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
In connection with an investigation being carried out in our laboratory on the influence of substituents on the course of reactions of halogenopyridines with potassium amide in liquid ammonia, the aminations of 2,3-, 2,4-, 2,5-, 3,4- and 3,5-dibromopyridine and of possible intermediate products, i.e., 4-amino-3-bromopyridine, the 5- and 6-bromo derivatives of 3-aminopyridine and the 3-, 4- and 5-bromo derivatives of 2-aminopyridine, have been studied. End-products are diaminopyridines or mixtures of these compounds and in some reactions a small amount of 4-amino-2-methylpyrimidine. The last-mentioned substance is the sole product isolated from the reaction mixture, obtained in the amination of 2,6-dibromopyridine3,4. The course of the aminations can be explained from what is known on the mechanisms of the aminations of the isomeric monobromopyridines and the mode of addition of ammonia to the triple bond in 3- and 4-substituted benzynes. For the formation of 4-amino-2-methylpyrimidine from 2,3-, 2,4- and 2,5-dibromopyridine a mechanism is suggested which is analogous to that assumed for the formation of that substance from 2,6-dibromopyridine3,4.