Pyrido(isoquinolino)-1,2,4-triazepines and pyrido(isoquinolino) pyrazolo-1,2,4triazepines were obtained from a reaction between o-diaminothioxocyclopentapyridine(isoquinoline), chalcones, diketones, esters, and aldehydes, respectively. It is shown that the more basic 1-NH2 (pyrido) and/or 2-NH2 (isoquinolino) group of the starting o-diamines participate in the formation of the azomethine bond of the seven-membered heteroring. Compounds (3, 6, 9, 12, 15, 17, and 19) are individual (TLC) and their structures are confirmed by the data from elemental analysis and spectroscopy.