Author(s):
Avijit Banerji, Rina Saha, Maya Gupta, Julie Banerji, Manosi Das, V. Subhose, P.V.V. Prasad
Email(s):
rinaasaha@gmail.com
DOI:
10.52711/0974-4150.2021.00042 
Address:
Avijit Banerji1,2*, Rina Saha2,3, Maya Gupta2, Julie Banerji2, Manosi Das1, V. Subhose1, P.V.V. Prasad1
1Central Ayurveda Research Institute, 4 Minerva Road, CN Block, Sector V, Kolkata 700091, West Bengal, India.
2Centre of Advanced Studies on Natural Products including Organic Synthesis
Department of Chemistry, University Colleges of Science and Technology, University of Calcutta, 92 Acharya Prafulla Chandra Road, Kolkata - 700009, West Bengal, India.
3Chemistry Department, Maharani Sudarshan College, Bikanir 334001, Rajasthan, India.
*Corresponding Author
Published In:
Volume - 14,
Issue - 4,
Year - 2021
ABSTRACT:
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.
Cite this article:
Avijit Banerji, Rina Saha, Maya Gupta, Julie Banerji, Manosi Das, V. Subhose, P.V.V. Prasad. Synthesis of 3,3′- Di-indolylmethanes under mild conditions by Microwave Irradiation Mediated Reactions of Indoles with C, N-Diaryl nitrones. Asian Journal of Research in Chemistry. 2021; 14(4):247-4. doi: 10.52711/0974-4150.2021.00042
Cite(Electronic):
Avijit Banerji, Rina Saha, Maya Gupta, Julie Banerji, Manosi Das, V. Subhose, P.V.V. Prasad. Synthesis of 3,3′- Di-indolylmethanes under mild conditions by Microwave Irradiation Mediated Reactions of Indoles with C, N-Diaryl nitrones. Asian Journal of Research in Chemistry. 2021; 14(4):247-4. doi: 10.52711/0974-4150.2021.00042 Available on: https://ajrconline.org/AbstractView.aspx?PID=2021-14-4-3
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