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Formation of oligomeric and macrocyclic ureas based on 2,6-diaminopyridine

Andrea Gube1, Hartmut Komber, Karin Sahre

  • 1Leibniz Institute of Polymer Research Dresden e.V. Hohe Straße 6, 01069 Dresden, Germany.

The Journal of Organic Chemistry
|October 18, 2012
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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