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Bronsted acid-catalyzed rapid enol-ether formation of 2-hydroxyindole-3-carboxaldehydes

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Abstract

A one-step Bronsted acid-catalyzed synthetic methodology leading to 3-(alkoxymethylene)indolin-2-ones was developed starting from easily accessible 2-hydroxyindole-3-carboxaldehydes. The procedure simply involves a treatment of differently substituted 2-hydroxyindole-3-carboxaldehydes with various alcohols (primary/secondary/tertiary/allyl/propargyl/benzyl) in the presence of a catalytic amount of Bronsted acids such as \(p\)-toluenesulfonic acid and trifluroacetic acid. A series of 19 indolin-2-one-based enol-ethers were synthesized in excellent yields, which implies the general character of our methodology. The enol-ethers produced could be used as a useful building block for the synthesis of indole-based heterocycles.

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Fig. 1
Scheme 1
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Acknowledgments

The authors gratefully acknowledge the financial support provided by Natural Sciences and Engineering Research Council of Canada (NSERC), Nipissing University, and the Canada Foundation for Innovation (CFI) to conduct this research.

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Authors and Affiliations

  1. Department of Biology and Chemistry, Nipissing University, North Bay, ON, P1B 8L7, Canada

    Darian Blanchard & Mukund Jha

  2. Department of Chemistry, Dalhousie University, Halifax, NS, B3H 4J3, Canada

    T. Stanley Cameron

Authors
  1. Darian Blanchard
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  2. T. Stanley Cameron
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  3. Mukund Jha
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Correspondence to Mukund Jha.

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Blanchard, D., Cameron, T.S. & Jha, M. Bronsted acid-catalyzed rapid enol-ether formation of 2-hydroxyindole-3-carboxaldehydes. Mol Divers 17, 827–834 (2013). https://doi.org/10.1007/s11030-013-9470-x

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  • DOI: https://doi.org/10.1007/s11030-013-9470-x

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