Condensed isoquinolines. 21. Condensation of o-bromomethylphenylacetonitrile with substituted anthranilic acids

Abstract

The reaction of substituted anthranilic acids and esters with o-bromomethylphenylacetonitrile give 2,3-R,R1-7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one hydrobromides. It was found that 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones can exist in the two tautomeric imine and enamine forms. The tautomeric equilibrium position depends on the nature and position of the substituent in the quinazoline fragment. The borohydride reduction, oxidation, and reaction of 2,3-R,R1-7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones with electrophilic reagents has been studied.