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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Synthesis of pharmacologically relevant indoles with amine side chains via tandem hydroformylation/Fischer indole

Axel M Schmidt1, Peter Eilbracht

  • 1Fachbereich Chemie, Organische Chemie I, Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund.

The Journal of Organic Chemistry
|July 2, 2005
PubMed

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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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