'One-flask' transformation of isocyanates and isothiocyanates to guanidines hydrochloride by using sodium bis(trimethylsilyl)amide

Chun Yen Chen, Hui Chang Lin, Yu Ying Huang, Kun Lung Chen, Jiann Jyh Huang, Mou Yung Yeh, Fung Fuh Wong

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15 Citations (Scopus)

Abstract

A 'one-flask' synthesis of guanidines was developed by reacting isocyanates and isothiocyanates with sodium bis(trimethylsilyl)amide followed by addition of primary or secondary amines with a catalytic amount of AlCl3. The desired guanidines were obtained in good yields and the reaction was applicable to aliphatic and aromatic substrates. A plausible mechanism was proposed through the generation of cyanamide anion from isocyanates or isothiocyanates with sodium bis(trimethylsilyl)amide. Addition of amines and catalytic amount of AlCl3 smoothly converted the cyanamides to the desired guanidines.

Original languageEnglish
Pages (from-to)1892-1897
Number of pages6
JournalTetrahedron
Volume66
Issue number10
DOIs
Publication statusPublished - 2010 Mar 6
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Chen, C. Y., Lin, H. C., Huang, Y. Y., Chen, K. L., Huang, J. J., Yeh, M. Y., & Wong, F. F. (2010). 'One-flask' transformation of isocyanates and isothiocyanates to guanidines hydrochloride by using sodium bis(trimethylsilyl)amide. Tetrahedron, 66(10), 1892-1897. https://doi.org/10.1016/j.tet.2010.01.003