One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement

Chien Hong Wang, Tsung Han Hsieh, Chia Chi Lin, Wen Hsiung Yeh, Chih An Lin, Tun Cheng Chien

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Abstract

Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.

Original languageEnglish
Article numberst-2015-u0285-l
Pages (from-to)1823-1826
Number of pages4
JournalSynlett
Volume26
Issue number13
DOIs
Publication statusPublished - 2015 Aug 12

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Keywords

  • Tiemann rearrangement
  • amidoxime
  • cyanamide
  • hydrolysis
  • urea

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Wang, C. H., Hsieh, T. H., Lin, C. C., Yeh, W. H., Lin, C. A., & Chien, T. C. (2015). One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement. Synlett, 26(13), 1823-1826. [st-2015-u0285-l]. https://doi.org/10.1055/s-0034-1381007