Issue 13, 2009
From the journal:

Organic & Biomolecular Chemistry

Facile two-step synthesis of 3-substituted indazoles using diazo(trimethylsilyl)methylmagnesium bromide†

Yoshiyuki Hari,*a   Ryosuke Soneb  and  Toyohiko Aoyama*b  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka, Japan
E-mail: hari@phs.osaka-u.ac.jp
Fax: +81 6 6879 8201
Tel: +81 6 6879 8201

b Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho, Nagoya, Japan
E-mail: aoyama@phar.nagoya-cu.ac.jp
Fax: +81 52 836 3439
Tel: +81 52 836 3439

Abstract

Diazo(trimethylsilyl)methylmagnesium bromide readily reacted with various ketones and aldehydes to give the corresponding 2-diazo-(2-trimethylsilyl)ethanols. These were efficiently converted to indazoles bearing hydroxymethyl units at the 3-position by intermolecular [3 + 2] cycloaddition with benzynes.

Graphical abstract: Facile two-step synthesis of 3-substituted indazoles using diazo(trimethylsilyl)methylmagnesium bromide

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Article information

DOI
https://doi.org/10.1039/B907796K
Article type
Paper
Submitted
17 Apr 2009
Accepted
17 Apr 2009
First published
22 May 2009

Org. Biomol. Chem., 2009,7, 2804-2808

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Facile two-step synthesis of 3-substituted indazoles using diazo(trimethylsilyl)methylmagnesium bromide

Y. Hari, R. Sone and T. Aoyama, Org. Biomol. Chem., 2009, 7, 2804 DOI: 10.1039/B907796K

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