Synthesis of 3,3′- Di-indolylmethanes under mild conditions by Microwave Irradiation Mediated Reactions of Indoles with C, N-Diaryl nitrones

吲哚试验 催化作用 化学 产量(工程) 三氟甲磺酸 甲苯 有机化学 芳基 二氯甲烷 干介质反应 药物化学 核化学 反应级数 材料科学 溶剂 物理 量子力学 反应速率常数 动力学 烷基 冶金
作者
Avijit Banerji,Rina Saha,Maya Gupta,Julie Banerji,Manosi Das,V. Subhose,Pulaganti Vijaya Prasad
出处
期刊:International research journal of pharmacy [Diva Enterprises Private Limited]
卷期号:: 247-254 被引量:2
标识
DOI:10.52711/0974-4150.2021.00042
摘要

3,3′-Di-indolylmethane derivatives are important biologically active compounds possessing anti-cancer properties. Hence, development of synthetic routes to these are of great interest to organic chemists. In the present communication we report a high-yield method using mild reaction conditions and short reaction times for the synthesis of 3,3′-di-indolylmethane derivatives. The method involved reactions of indole and substituted indoles with C,N-disubstituted nitrones in the presence of acid catalysts, with the utilisation of microwave irradiation techniques. Reactions of indole, 2-methyl indole and 2-phenyl indole were performed with ten different C,N-diaryl- and C-aryl-N-methyl- nitrones in dichloromethane solution in the absence and presence of acid catalysts, viz. ytterbium triflate, p-toluene sulphonic acid and Montmorillonite clay K-10. Reaction times varied between 2 to 18 minutes. In general, yields of the catalysed reactions were above 75%. The products were characterised spectroscopically, including two-dimensional NMR studies. The microwave irradiation technique enhanced reaction rates by a significant amount. Ytterbium triflate proved to be the best catalyst, giving clean reactions, without formation of by-products, in high yields. The structure and conformation of 3,3′-di-indolyl-phenylmethane were computed. GRAPHICAL ABSTRACT: We report a high-yield method using mild reaction conditions and short reaction times for the synthesis of 3,3′-di-indolylmethane derivatives, involving reactions of indole and substituted indoles with C, N-disubstituted nitrones in the presence of acid catalysts using microwave irradiation.

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