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The syntheses of several polyazaheterocycles are demonstrated. The cyclocondensation reactions between β-enaminodiketones [CCl 3 C(O)C(=CNMe 2 )C(O)-CO 2 Et] and aromatic amidines resulted in glyoxalate-substituted pyrido[1,2- a ]pyrimidinone, thiazolo[3,2- a ]pyrimidinone and pyrimido[1,2- a ]benzimidazole. Pyrazinones and quinoxalinones were obtained through the reaction of these glyoxalates with ethylenediamine and 1,2-phenylenediamine derivatives. On the other hand, the reaction of glyoxalates with amidines did not lead to the formation of imidazolones, but rather N -acylated products were obtained. All the products were isolated in good yields. DFT-B3LYP calculations provided HOMO/LUMO coefficients, charge densities, and the stability energies of the intermediates, and from these data it was possible to explain the regiochemistry of the products obtained. Additionally, the data were a useful tool for elucidating the reaction mechanisms.

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles