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Synthesis 1990; 1990(9): 803-808
DOI: 10.1055/s-1990-27021
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Rearrangement of 3,3-Disubstituted 1-Aryl-4,5-dihydro-5-oxo-3H-1,2,4-triazolium Tetrafluoroborates; Part 1. A Versatile Synthesis of 1,5-Disubstituted 2-Aryl-1,2-dihydro-3H-1,2,4-triazol-3-one Tetrafluoroborates

Hubert Gstach* , Patrick Seil
  • *Institut für Organische und Pharmazeutische Chemie, Universität Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria
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Publication Date:
17 September 2002 (online)

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α-(Arylazo)alkyl isocyanates 3 react with tetrafluoroboric acid to yield 3, 3-disubstituted 1-aryl-4,5-dihydro-5-oxo-3H-1,2,4-triazo-lium tetrafluoroborates 4. These compounds rearrange under mild conditions and in good yields to the tetrafluoroborates of 1,5 disubstituted 2-aryl-1,2-dihydro-3H-1,2, 4-triazol-3-ones 5. Our results show that the nature of the substituents determines their migratory aptitude for the rearrangement.