4.5 Article

Highly Efficient Synthesis of Ureas and Carbamates from Amides by Iodosylbenzene-Induced Hofmann Rearrangement

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 10, Pages 1994-2000

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101784

Keywords

Heterocycles; Amides; Oxidation; Rearrangement

Funding

  1. Important National Science & Technology Specific Projects, China [2009ZX09301-14-1]
  2. National Natural Science Foundation of China [21102107]
  3. China Postdoctoral Science Foundation [20110491199]

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A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98?% yield. Ureidopeptides can also be prepared in good yield by this method.

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