Flash vacuum pyrolysis of azolylacroleins and azolylbutadienes

Paola L. Lucero, Walter J. Peláez, Zsuzsanna Riedl, György Hajós, Elizabeth L. Moyano, Gloria I. Yranzo

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9 Citations (Scopus)

Abstract

2-Aryl-5-acroleinyl-1,2,3,4-tetrazoles (1a-d) and 2-aryl-5-butadienyl-1,2, 3,4-tetrazoles (1e-g) were subjected to flash vacuum pyrolysis. Acroleinyl derivatives resulted in nitrogen extrusion to give nitrilimines followed by ring closure to give the corresponding indazoles 3a-d in good yields. On the other hand, butadiene derivatives underwent ring fragmentation to give p-substituted anilines without formation of the expected indazoles. Differences between thermal behaviour of 2-(4-chlorophenyl)-5-acroleinyl-1,2,3,4-tetrazole (1c) and 1-(4-chlorophenyl)-4-acroleinyl-1,2,3-triazole (2) were studied in details. DFT calculations have been used to examine the nitrilimine and carbene nature of the intermediates involved in the thermal reactions of azolyl derivatives.

Original languageEnglish
Pages (from-to)1299-1305
Number of pages7
JournalTetrahedron
Volume68
Issue number4
DOIs
Publication statusPublished - Jan 28 2012

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Keywords

  • Indazole
  • Nitrilimine
  • Nitrogen extrusion
  • Pyrolysis
  • Tetrazole

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Lucero, P. L., Peláez, W. J., Riedl, Z., Hajós, G., Moyano, E. L., & Yranzo, G. I. (2012). Flash vacuum pyrolysis of azolylacroleins and azolylbutadienes. Tetrahedron, 68(4), 1299-1305. https://doi.org/10.1016/j.tet.2011.11.034