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Synthesis of potential fungicides based on N-(3-furanyl)pyrrolecarboxamides and N-(3-furanyl)pyrazolecarboxamides

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Abstract

An efficient synthesis of novel N-(3-furanyl)pyrrolecarboxamides and N-(3-furanyl)pyrazolecarboxamides is presented starting from furan-3-carboxylic acid. Two complementary strategies to 2-aryl-3-furanamines with directed ortho lithiation, functionalization of the 2-position, and subsequent cross-coupling reaction as key steps were developed. Acylation of these intermediates with appropriate acid chlorides led finally to the target compounds.

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Acknowledgments

We thank Syngenta Crop Protection, Basel, for financial support of this project and for providing acids 10a and 10b.

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Authors and Affiliations

  1. Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060, Vienna, Austria

    Krzysztof Kolodziejczyk, Michael Schnürch, Marko D. Mihovilovic & Peter Stanetty

  2. Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, 11 Arany Janos Street, 400028, Cluj-Napoca, Romania

    Gheorghe D. Roiban

Authors
  1. Krzysztof Kolodziejczyk
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  2. Gheorghe D. Roiban
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  3. Michael Schnürch
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  4. Marko D. Mihovilovic
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  5. Peter Stanetty
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Correspondence to Michael Schnürch.

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Kolodziejczyk, K., Roiban, G.D., Schnürch, M. et al. Synthesis of potential fungicides based on N-(3-furanyl)pyrrolecarboxamides and N-(3-furanyl)pyrazolecarboxamides. Monatsh Chem 140, 1349–1359 (2009). https://doi.org/10.1007/s00706-009-0187-6

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  • DOI: https://doi.org/10.1007/s00706-009-0187-6

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