Conventional and microwave-assisted conversion of substituted 3-amino-oxazolidin-2,4-diones into N',N'-disubstituted

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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

Thomas Kurz1, Khalid Widyan

  • 1Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, 20146 Hamburg, Germany. kurz@chemie.uni-hamburg.de

The Journal of Organic Chemistry
|April 13, 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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