A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N-benzyl matemone

Makoto Shimizu; Hayao Imazato; Isao Mizota; Yusong Zhu

doi:10.1039/C9RA02204J

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A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N-benzyl matemone†

Makoto Shimizu,

*^ab Hayao Imazato,^b Isao Mizota^b and Yusong Zhu^a

Author affiliations

* Corresponding authors

^a School of Energy Science and Engineering, Nanjing Tech University, Nanjing 211816, Jiangsu Province, China

^b Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan
E-mail: mshimizu@chem.mie-u.ac.jp

Abstract

2-Alkoxycarbonylindolin-3-one is synthesized from a methoxyglycine derivative via a 1,2-aza-Brook rearrangement followed by cyclization with bis(trimethylsilyl)aluminum chloride. A short-step synthesis of N-benzyl matemone is successfully carried out using the present indolin-3-one synthesis.

This article is part of the themed collection: Elegant Synthetic Routes to Indole Derivatives

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Article information

DOI: https://doi.org/10.1039/C9RA02204J
Article type: Paper
Submitted: 21 Mar 2019
Accepted: 27 May 2019
First published: 03 Jun 2019
This article is Open Access

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RSC Adv., 2019,9, 17341-17346

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A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N-benzyl matemone

M. Shimizu, H. Imazato, I. Mizota and Y. Zhu, RSC Adv., 2019, 9, 17341 DOI: 10.1039/C9RA02204J

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A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N-benzyl matemone†

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A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N-benzyl matemone

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