Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
A Study on the Mechanism of the Dimerization of Quinazoline Compounds Catalyzed by Cyanide Ions
Ayako GotoTakeo Higashino
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1986 Volume 59 Issue 2 Pages 395-398

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Abstract

It was shown that an intermediate, 4,4′(3H,3′H)-biquinazolinylidene (2a) was isolated in the formation process of 4,4′-biquinazolinyl (3a) which was obtained from the reaction of quinazoline (1a) with potassium cyanide, and 2a was readily oxidized to 3a by oxygen in air. The dimerization process was studied kinetically by NMR method. The result showed that the process was essentially similar to that of the benzoin condensation. The introduction of a methyl group into the C2-position of 1a resulted in a lowering of the reaction rate because the activation energy of 2-methylquinazoline (1b) dimerization became higher compared with that of 1a dimerization.

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