STUDIES ON QUINAZOLINE CHEMISTRY. 5. SYNTHESIS OF 3,4-DIHYDROQUINAZOLINES WITH FUNCTIONAL SUBSTITUENTS AT C-2 ATOM AND THEIR ALKYLATION REACTIONS

Abstract

Syntheses are reported for a new series of 2-substituted 4,4-diphenyl-3,4-dihydroquinazolines by the reaction of o-aminophenyldiphenylcarbinol (APC) with various nitriles. The reaction of APC with substituted 5-bromo-3-cyano-2(1H)-pyridones leads to the formation of derivatives of two products: 3,4-dihydroquinazolines and 4H-3,1-benzoxazines. The alkylation of 3,4-dihydroquinazolines using dimethyl sulfate proceeds through N,N-dimethylation. The structure of these products is a function of the nature of the substituent at C-2 atom of the heterocycle.

Authors: E. V. Gromachevskaya, E. A. Kaigorodova, K. S. Pushkareva, and G. D. Krapivin

English Translation in Chemistry of Heterocyclic Compounds, 2013, 48 (10), pp 1492-1502

http://link.springer.com/article/10.1007/s10593-013-1163-y