Tolkunov A. Heteroannelated 1,2-diazepines and 1,2-diazocines. Synthesis and properties

A general method for the synthesis of fused 1,2-diazepines and 1,2-diazocines, based on the Pictet-Spengler reaction of N-aminoheterocycles with carbonyl compounds, was proposed. By the reaction of carbonyl compounds with 3-amino-2-arylmethylquinazolin-4(3Н)-ones and 3-amino-2-(3,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidin-4(3Н)one new fused heterocyclic systems were synthesized: 11,12-dihydro-quinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones and 7,12-dihydrothieno[2',3':4,5]pyri-mido[1,2-с][2,3]benzodiazepin-4(6Н)-ones. For the first time by the interaction between corresponding 3-amino-2-hetarylmethylquinazolin-4(3H)-ones new fused 1,2-diazepines were obtained: 6,15-di-hydrobenzothieno[2',3':4,5][1,2]diazepino[7,1-b]quinazolin-9(7H)-ones, 6,15-dihydro-benzofuro[2',3':4,5][1,2]diazepino[7,1-b]quinazolin-9(7H)-ones and 5,6,7,15-tetrahydro-9H-indolo[2',3':4,5][1,2]diazepino[7,1-b]quinazolin-9-ones. A new easy method for the synthesis of 6,11-dihydro-5H-[1,2,4]triazolo[4,3-с][2,3]benzodiazepines and 6,12-dihydro-7H-benzothieno[3,2-e][1,2,4]triazolo[4,3-b][1,2]diazepines was proposed based on the interaction between corresponding 4-aminotriazoles with carbonyl compounds in acidic medium. By the reaction between 3-amino-2-[2-(3,4-dimethoxyphenyl)ethyl]quinazolin-4(3Н)-one and carbonyl compounds in acidic medium a new fused eight-membered heterocyclic system was obtained - 6,7,12,13-tetrahydro-15H-quinazolino[3,2-с][2,3]-benzodiazocin-15-ones. The oxidation of C-N-bond in 8,9-dimethoxy-11-R-11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones and 7,12-dihydrothieno[2',3':4,5]pyrimido[1,2-с][2,3]benzodiazepin-4(6Н)-ones was carried out by the reaction with chromic anhydride in acetic acid.