Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence

Akira Nakamura; Satoshi Tanaka; Akira Imamiya; Reo Takane; Chiaki Ohta; Kazuma Fujimura; Tomohiro Maegawa; Yasuyoshi Miki

doi:10.1039/C7OB01536D

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Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence†

Akira Nakamura,

^a Satoshi Tanaka,^a Akira Imamiya,^a Reo Takane,^a Chiaki Ohta,^a Kazuma Fujimura,^a Tomohiro Maegawa

*^a and Yasuyoshi Miki*^ab

Author affiliations

* Corresponding authors

^a School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan
E-mail: maegawa@phar.kindai.ac.jp

^b Research Organization of Science and Technology, Research Center for Drug Discovery and Pharmaceutical Science, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan

Abstract

An efficient one-pot method was developed for the construction of 3-acylindoles via oxidative rearrangement of 2-aminochalcones followed by intramolecular cyclization. The reaction was used to convert a variety of 2-aminochalcones into 3-acylindoles in moderate to high yields.

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Article information

DOI: https://doi.org/10.1039/C7OB01536D
Article type: Communication
Submitted: 24 Jun 2017
Accepted: 19 Jul 2017
First published: 19 Jul 2017

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Org. Biomol. Chem., 2017,15, 6702-6705

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Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence

A. Nakamura, S. Tanaka, A. Imamiya, R. Takane, C. Ohta, K. Fujimura, T. Maegawa and Y. Miki, Org. Biomol. Chem., 2017, 15, 6702 DOI: 10.1039/C7OB01536D

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Organic & Biomolecular Chemistry

Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence†

Abstract

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Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence

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