Object of the investigation is benzofuro[2,3-d][1,2]diazepin-4-ones, benzothieno[2,3-d][1,2]diazepin-4-ones, [1,2]diazepino[4,5-b]indol-4-ones, and tetrahydrobenzofuro(tetrahydro benzothieno)[2,3-c]pyridines. Aim of the investigation - to design methods for synthesis of benzofuro[2,3-d][1,2]diazepin-4-ones, benzothieno[2,3-d][1,2]diazepin-4-ones, and [1,2]diazepino[4,5-b]indol-4-ones as well as to investigate their chemical properties by the example of benzofuro[2,3-d][1,2]diazepin-4-ones. Methods of the investigation are methods of organic synthesis, elemental analysis, NMR 1H and 13C spectroscopy, mass and chromatography mass spectrometry, X-ray analysis. A general approach to the synthesis of benzofuro[2,3-d][1,2]diazepin-4-ones, benzothieno[2,3-d][1,2]diazepin-4-ones and [1,2]diazepino[4,5-b]indol-4-ones was proposed on the base of the heterocyclization of the 2-aroylbenzothiophen-3-acetic acids, 2-aroylbenzofuran-3-acetic acids, 2-aroylindolyl-3-acetic acids, as well as their esters with hydrazine hydrate in acidic catalysis conditions. Optimal conditions to carry out the reactions of alkylation, amination, and cyclocondensation of obtained diazepines were found, that allows to synthesize a wide spectrum of the [1,2]diazepin-4-one derivatives. For the first time product of С-5 diazepine ring substitution was obtained by 8-methyl-1-(4-chlorophenyl)-3,5-dihydro-4H-[1]benzofuro[2,3-d][1,2]diazepin-4-one alkylation. A new reaction of 6-(4-chlorophenyl)-1-(4-methoxyphenyl)-9-methyl-4H-[1]benzofuro[3,2-e]thieno[2,3-с][1,2]diazepine formation was revealed. One-step synthesis of 6-(4-chlorophenyl)-9-R-3-methyl-12H-[1]benzofuro[3,2-e][1,2,4]triazolo[4,3-b][1,2]diazepines was realized under silylation-amination reaction conditions. A new method to the synthesis of 1-R-1,2,3,4- tetrahydro[1]benzofuro(benzothieno)[2,3-c]pyridines was proposed on the base of Pictet-Spengler reaction in the presence of triisopropylchlorosilane and dimethylformamide. Results can be used for preparative synthesis of 1,2-diazepines, tetrahydro[2,3-c]pyridines derivatives, azocines, for design of new bioactive compounds.
