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A revisit to the multi-component reaction of indole, aldehyde, and N-substituted aniline catalyzed by PMA–SiO2

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Abstract

PMA–SiO2-catalyzed multi-component reaction of indole, aromatic aldehyde, and N-substituted aniline at room temperature under solvent-free condition is reported here. The reaction was previously reported, where a C–C and C–N bond were formed. However, we established a different structure for the product with the help of NMR as well as single-crystal X-ray studies, where the C-4 atom of N-substituted aniline is linked to the aldehydic carbon, and consequently, two new C–C bonds are formed. The mechanism of the reaction is established through trapping of the intermediate which is also different from the previous report. To the best of our knowledge, only one report is available in the literature for the synthesis of this class of important compounds.

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Acknowledgements

MLD is thankful to Science and Engineering Research Board (SERB), India (Grant no. SB/FT/CS-073/2014) for the financial support under “Fast Track” Scheme. PKB is also thankful to SERB, India (Grant no. SB/FT/CS-100/2012) for the financial support. We acknowledge Dr. S. Karmakar for collecting single-crystal X-ray data and the Sophisticated Analytical Instrumentation Facility (SAIF), GU, for the use of single-crystal X-ray diffractometer.

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Authors and Affiliations

  1. Department of Applied Sciences, GUIST, Gauhati University, Guwahati, Assam, 781014, India

    Bhaskar Deka, Mohit L. Deb & Pranjal K. Baruah

  2. Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India

    Ranjit Thakuria

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  1. Bhaskar Deka
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  2. Ranjit Thakuria
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  3. Mohit L. Deb
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  4. Pranjal K. Baruah
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Correspondence to Mohit L. Deb or Pranjal K. Baruah.

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Deka, B., Thakuria, R., Deb, M.L. et al. A revisit to the multi-component reaction of indole, aldehyde, and N-substituted aniline catalyzed by PMA–SiO2. Monatsh Chem 149, 2245–2252 (2018). https://doi.org/10.1007/s00706-018-2290-z

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  • DOI: https://doi.org/10.1007/s00706-018-2290-z

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