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Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds

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Abstract

2-Chloro-3-formyl quinoline has been applied as an aldehyde moiety in the Groebke–Blackburn–Bienaymé multi-component reaction with isocyanides, 2-aminoazines, and 2-aminoazole to afford the desired adducts which are amenable for further cyclization on the basis of Ullmann-type coupling. The copper iodide-mediated intramolecular C–N bond formation in the second step gave an easy access to a series of imidazo[4\('\),5\('\):4,5]pyrrolo[2,3-b]quinoline derivatives in moderate to good yields.

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Acknowledgments

This work was supported by grants from Tehran University of Medical Sciences and Iran National Science Foundation (INSF).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Shahid Chamran University, Ahvaz, Iran

    Shima Dianat & Arash Mouradzadegun

  2. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Mahdavi, Setareh Moghimi, Abbas Shafiee & Alireza Foroumadi

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  1. Shima Dianat
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  2. Mohammad Mahdavi
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  3. Setareh Moghimi
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  4. Arash Mouradzadegun
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  5. Abbas Shafiee
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  6. Alireza Foroumadi
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Correspondence to Alireza Foroumadi.

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Copies of 1H-NMR 13C-NMR spectra are available as supplementary data. (DOC 1,912 KB)

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Dianat, S., Mahdavi, M., Moghimi, S. et al. Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds. Mol Divers 19, 797–805 (2015). https://doi.org/10.1007/s11030-015-9622-2

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