Synthesis of 5-arylacetylene 1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions

  1. Andrey I. PuzanovORCID Logo,
  2. Dmitry S. RyabukhinORCID Logo,
  3. Anna S. Zalivatskaya,
  4. Dmitriy N. ZakusiloORCID Logo,
  5. Darya S. Mikson,
  6. Irina A. Boyarskaya and
  7. Aleksander VasilyevORCID Logo

Submitting author affiliation: Saint Petersburg State Forest Technical University, Saint Petersburg, Russian Federation

Beilstein Arch. 2021, 202149. https://doi.org/10.3762/bxiv.2021.49.v1

Published 30 Jun 2021

  • Preprint

Abstract

Acetylene derivatives of 1,2,4-oxadiazoles, 5-(2-arylethynyl)-3-aryl-1,2,4-oxadiazoles, have been obtained, for the first time, from 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles by their bromination at the carbon-carbon double bond followed by di-dehydrobromination with NaNH2 in liquid NH3.  Reaction of the acetylene 1,2,4-oxadiazoles with arenes in neat triflic acid TfOH (CF3SO3H) at room temperature for 1 h result in the formation of E-/Z-5-(2,2-diarylethenyl)-3-aryl-1,2,4-oxadiazoles as products of regioselective hydroarylation of the acetylene bond. Addition of TfOH to acetylene bond of these oxadiazoles gives rise quantitatively to E-/Z-vinyl triflates. Reaction cationic intermediates have been studied by DFT calculations. The reaction mechanisms have been discussed.

Keywords: acetylene oxadiazoles, hydroarylation, Friedel-Crafts reaction, superelectrophilic activation, triflic acid

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Puzanov, A. I.; Ryabukhin, D. S.; Zalivatskaya, A. S.; Zakusilo, D. N.; Mikson, D. S.; Boyarskaya, I. A.; Vasilyev, A. Beilstein Arch. 2021, 202149. doi:10.3762/bxiv.2021.49.v1

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