Khylya O. 3,4-Dihydro-4-оxo-2-quinazolylacetonitriles in the reactions of heterocyclization

The conditions of the synthesis of 2-cyanomethylquinazolones were elaborated and optimized. The tautomerism of these compounds was first identified. The direction of their alkylation was established. It was established that 6-chloro-2-(2-hetarylidene)-3-oxohexanenitriles undergo regioselective intramolecular alkylation under treatment of bases, leading to 2-(2-hetaryl)-2-(tetrahydro-2-furanyliden)acetonitriles. The interaction of 2-(2-hetaryl)-2-(tetrahydro-2-furanyliden)acetonitriles with nucleophiles was investigated and a facile route to the polyfunctional b-enaminonitriles and azoles was elaborated. It was established that the interaction of 2-hetarylacetonitriles with (hetero)aromatic о-haloaldehydes leads to the formation of tetra- and pentacyclic systems as a result of regioselective intramolecular (het)arylation.