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Synthesis of Isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepines via N-Acyliminium Cyclization

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Abstract

Fused polycyclic compounds with benzo[c]isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepine, dibenzo[c,e]isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepine, and benzo[f]isoxazolo[5',4':3,4]pyrrolo[1,2-d]oxazepine cores are readily available via cyclization of the N-acyliminium cation generated from the corresponding 6-hydoxy-5-R-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazol-4(5H)-ones in the presence of BF3·Et2O or Sn(NTf2)4.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Magnetic Resonance and Chemical Analysis and Materials Research Centers and Chemistry Educational Center, St. Petersburg State University.

Funding

O.B. Chakchir and V.M. Boitsov are grateful to the Ministry of Education and Science of the Russian federation for financial support (project no. 16.9790.2017/BCh) for financial support.

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Authors and Affiliations

  1. St. Petersburg State University, 199034, St. Petersburg, Russia

    L. V. Lenshmidt, M. S. Ledovskaya, A. G. Larina, A. S. Filatov & A. V. Stepakov

  2. St. Petersburg Academic University, 194021, St. Petersburg, Russia

    O. B. Chakchir

  3. Voeikov Main Geophysical Observatory, 194021, St. Petersburg, Russia

    A. A. Uspenskii & A. V. Stepakov

Authors
  1. L. V. Lenshmidt
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  2. M. S. Ledovskaya
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  3. A. G. Larina
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  5. O. B. Chakchir
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Correspondence to A. V. Stepakov.

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Lenshmidt, L.V., Ledovskaya, M.S., Larina, A.G. et al. Synthesis of Isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepines via N-Acyliminium Cyclization. Russ J Org Chem 56, 234–245 (2020). https://doi.org/10.1134/S1070428020020098

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