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Synthesis of 3-substituted indole by AlCl3-promoted reaction of β,γ-unsaturated ketone with indole

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Abstract

A one-pot Lewis acid-promoted reaction condition of β,γ-unsaturated ketone with indole was developed for the synthesis of 3-substituted indoles with moderate to good yields. A Lewis acid such as AlCl3 was shown to be a promising promoter for in situ isomerization of β,γ-unsaturated ketone to its corresponding α,β-unsaturated ketone, then undergoing Friedel–Crafts Michael addition reaction with indole to afford 3-substituted indole.

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Acknowledgments

We thank the National Science Council in Taiwan (NSC 101-2113-M-032-003) and Tamkang University for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Tamkang University, New Taipei, 251, Taiwan

    Adam Shih-Yuan Lee, Yu-Chi Wu, Yu-Ting Chang & Bo-Cheng Wang

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  1. Adam Shih-Yuan Lee
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  2. Yu-Chi Wu
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  3. Yu-Ting Chang
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  4. Bo-Cheng Wang
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Correspondence to Adam Shih-Yuan Lee.

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Lee, A.SY., Wu, YC., Chang, YT. et al. Synthesis of 3-substituted indole by AlCl3-promoted reaction of β,γ-unsaturated ketone with indole. Res Chem Intermed 40, 2277–2285 (2014). https://doi.org/10.1007/s11164-014-1605-x

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