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.

中文翻译：

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邻苯二胺作为稠合唑、氮和二氮杂衍生物的来源

摘要

通过从邻苯二胺和苯乙酮获得的烯胺 [ N ¹ -(1-苯基乙烯基)苯-1,2-二胺]的反应开发了一种简便的二氮杂和/或苯并咪唑衍生物合成方法。它与间苯二甲酰氯反应生成双（1,5-苯并二氮杂）苯衍生物，通过涉及亲核烯氨基碳原子的环化，而与琥珀酸二乙酯在亲核氮原子上发生环缩合反应生成双苯并咪唑衍生物。根据条件，在 DMSO 中与二硫化碳环化得到三环 4-苯基咪唑并[4,5,1 - hi ]indole-2(1 H )-硫酮，而 4-苯基-1,3-dihydro-2 H-1,5-苯二氮卓-2-硫酮在吡啶存在下形成。在酸性介质中邻苯二胺与两当量苯乙酮的环缩合反应生成 3-苯基-1-(1-苯基乙烯基)-1,4-二氢喹喔啉。由邻苯二胺和硫氰酸铵得到的N- (2-氨基苯基)硫脲与氯乙酰氯、丙二酸二乙酯、二硫化碳和亚硝酸钠在 HCl 水溶液中反应，得到苯并咪唑、噻二唑并苯并咪唑和苯并三唑衍生物。