Paper
Facile two-step synthesis of 3-substituted indazoles using diazo(trimethylsilyl)methylmagnesium bromide.
Published Jun 17, 2009 · Y. Hari, Ryosuke Sone, T. Aoyama
Organic & biomolecular chemistry
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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.
Diazo(trimethylsilyl)methylmagnesium bromide is a convenient and efficient method for synthesising 3-substituted indazoles with hydroxymethyl units at the 3-position.
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