Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds

  • Ng E
  • Wang Y
  • Hui B
 et al. 
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Abstract

Tri- and tetrasubstituted N-H pyrroles were prepared by the simple treatment of vinyl azides with 1,3-dicarbonyl compounds in toluene at 100 °C via 2H-azirine intermediates generated in situ. When the reactions of vinyl azides and 1,3-dicarbonyl compounds were performed in DMF in the presence of a catalytic amount of K2CO3, 1-vinyl-1,2,3-triazoles were obtained via 1,3-dipolar cycloaddition. These methodologies exploited orthogonal modes of chemical reactivity of vinyl azides, which could be achieved by slight modification of the reaction conditions. © 2011 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • 1,2,3-Triazoles
  • 1,3-Dicarbonyl compounds
  • Pyrroles
  • Vinyl azides

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Authors

  • Eileen Pei Jian Ng

  • Yi Feng Wang

  • Benjamin Wei Qiang Hui

  • Guillaume Lapointe

  • Shunsuke Chiba

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