41054-45-9Relevant articles and documents
o-Phenylenediamine as a Source of Fused Azole, Azine, and Diazepine Derivatives
Almostafa, A. M.,Assy, M. G.,Ismail, N. A.,Shehta, W.
, p. 1152 - 1157 (2021/09/08)
Abstract: A facile synthetic approach to diazepine and/or benzimidazole derivatives has been developed through the reaction of enamine [N1-(1-phenylethenyl)benzene-1,2-diamine] obtained from o-phenylenediamine and acetophenone. Its reaction with isophthaloyl chloride produced bis(1,5-benzodiazepinyl)benzene derivative via cyclization involving the nucleophilic enamino carbon atom, whereas the cyclocondensation with diethyl succinate occurred at the nucleophilic nitrogen atom to give bis-benzimidazole derivative. Depending on the conditions, the cyclization with carbon disulfide in DMSO afforded tricyclic 4-phenylimidazo[4,5,1-hi]indole-2(1H)-thione, while 4-phenyl-1,3-dihydro-2H-1,5-benzodiazepine-2-thione was formed in the presence of pyridine. Cyclocondensation of o-phenylenediamine with two equivalents of acetophenone in acid medium produced 3-phenyl-1-(1-phenylethenyl)-1,4-dihydroquinoxaline. N-(2-Aminophenyl)thiourea obtained from o-phenylenediamine and ammonium thiocyanate reacted with chloroacetyl chloride, diethyl malonate, carbon disulfide, and sodium nitrite in aqueous HCl to afford benzimidazole, thiadiazolobenzimidazole, and benzotriazole derivatives.
SYNTHESIS AND MASS SPECTRA OF 2,3-DIHYDRO-1H-1,5-BENZODIAZEPINE-2-THIONES
Solomko, Z. F.,Sharbatyan, P. A.,Gaponov, A. A.,Avramenko, V. I.
, p. 341 - 345 (2007/10/02)
2,3-Dihydro-1H-1,5-benzodiazepine-2-thiones and their N-methyl and S-methyl derivatives were synthesized.It was demonstrated by means of the IR, UV, PMR, and mass spectra that in solutions with different polarities 1,5-benzodiazepine-2-thiones exist prima