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An efficient, general synthesis of 2-substituted 3,6-dihydropyrrolo[3,2-e]indoles involving one-pot Sonogashira coupling and cyclisation

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Abstract

A number of 2-substituted 3,6-dihydropyrrolo[3,2-e]indoles were synthesised efficiently by the reaction of 4-iodo-1-(phenylsulfonyl)-5-(trifluoroacetamido)indole with terminal acetylenes in the presence of a palladium(0) catalyst and a copper(I) co-catalyst. The reaction involved one-pot Sonogashira coupling/heteroannulation, the first one of its kind in the synthesis of the title compounds. The required amido-iodoindole was prepared smoothly from 5-nitroindole by successive N-protection, reduction of the nitroarene, iodination of the resulting aminoarene and N-trifluoroacetylation.

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Acknowledgments

Professor M. Chakrabarty, Emeritus Scientist, thanks the Director of Bose Institute for laboratory facilities and the Council of Scientific and Industrial Research (CSIR), Govt. of India, for financial assistance (Sanction no. 21(824)/10/EMR-II, dated 23.12.2010). Professor G. K. Kar and Mrs. M. Rakshit are thankful to the CSIR, Govt. of India, for providing CSIR-NET fellowship to M. Rakshit. All the authors are thankful to Mr. B. Majumdar and Mr. S. R. Maji, both of Bose Institute, for recording NMR and GC HR-MS spectra, respectively.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, Presidency University (formerly Presidency College), 86/1, College Street, Kolkata, 700073, India

    Moumita Rakshit & Gandhi K. Kar

  2. Department of Chemistry, Bose Institute, 93/1, A.P.C. Road, Kolkata, 700009, India

    Manas Chakrabarty

  3. Department of Chemistry, NIT Sikkim, Ravangla, South Sikkim, 737139, India

    Taraknath Kundu

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  1. Moumita Rakshit
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  2. Taraknath Kundu
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  3. Gandhi K. Kar
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  4. Manas Chakrabarty
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Correspondence to Gandhi K. Kar.

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Rakshit, M., Kundu, T., Kar, G.K. et al. An efficient, general synthesis of 2-substituted 3,6-dihydropyrrolo[3,2-e]indoles involving one-pot Sonogashira coupling and cyclisation. Monatsh Chem 144, 717–724 (2013). https://doi.org/10.1007/s00706-012-0859-5

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  • DOI: https://doi.org/10.1007/s00706-012-0859-5

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