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Efficient one-pot synthesis of new 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate esters via copper-free Sonogashira coupling reactions

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Abstract

The reactions of several 2-chloroquinoline-3-carboxylate esters with propargyl alcohol and a secondary amine in the presence of palladium catalyst leads to the formation of new alkyl 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate derivatives. This one-pot process, carried out in the absence of any copper salt, provides an efficient method for the synthesis of functionalized pyrrolo[1,2-a]quinolines in good-to-high yields.

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Acknowledgments

We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

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Authors and Affiliations

  1. School of Chemistry, Shahrood University of Technology, Shahrood, Iran

    Ali Keivanloo, Shaghayegh Sadat Kazemi & Hossein Nasr-Isfahani

  2. Chemistry Faculty, University of Kashan, Kashan, Iran

    Abdolhamid Bamoniri

Authors
  1. Ali Keivanloo
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  2. Shaghayegh Sadat Kazemi
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  3. Hossein Nasr-Isfahani
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  4. Abdolhamid Bamoniri
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Correspondence to Ali Keivanloo.

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11030_2016_9694_MOESM1_ESM.docx

The supporting information for this work is available, as follows: copies of 1H and 13C spectra of all the 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate esters.(doc 1.83MB)

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Keivanloo, A., Kazemi, S.S., Nasr-Isfahani, H. et al. Efficient one-pot synthesis of new 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate esters via copper-free Sonogashira coupling reactions. Mol Divers 21, 29–36 (2017). https://doi.org/10.1007/s11030-016-9694-7

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