The interaction of 7-amino-4-methyl-1-R1-5-R2-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones with β-unsaturated ketones – dimethyl-2-oxoglutaconate and methyl-4-oxo-2-pentenoate was investigated in the conditions of the modified Doebner-Miller reaction. Four-membered derivatives of the new fused heterosystem – 4,8-dioxo-6,7,8,9-tetrahydro-4H-[1,4]diazepino[3,2,1-hi]pyrido[4,3,2-cd]indole were synthesized by the condensation of 7-amino-4-methyl-1-R1-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones (5-R2 = H) with dimethyl-2-oxoglutaconate. By the interaction of 7-amino-4-methyl-5-alkyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones with oxoglutaconate, tricyclic 2-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[2,3-g]quinolines were obtained. The reaction of 7-amino-1-methyl(or 5-methyl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones and methyl-4-oxopentenoate occured to form 10-methylsubstituted [1,4]diazepino[2,3-g]quinoline derivatives. It was established that the direction of cyclization and the structure of the polycyclic products depend on the presence of substituents at the 1- and 5-positions of starting amines and on the structure of α, β-unsaturated ketone.