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Intramolecular heterocyclization of o-(1-cycloalkenyl)anilines 2*. Synthesis of new 4Н-3,1-benzoxazine and 4Н-3,1-benzothiazine 2-amino derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A new method was developed to synthesize 2-amino derivatives of 3,1-benzoxazines and 3,1-benzothiazines on the basis of о-(cyclopent-1-en-1-yl)aniline by heterocyclization of phenyl- and allylurea and thiourea derivatives in the presence of CF3CO2H, H2O2, or Br2.

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This work was performed on the topics of State Assignments АААА-А19-119011790021-4 and АААА-А17-117011910027-0.

NMR spectra were acquired using the equipment of the Collective Use Center “Chemistry” of the Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa, 450054, Russia

    Shamil M. Salikhov, Lyaisan R. Latypova & Ildus B. Abdrakhmanov

  2. Bashkir State Agrarian University, 34 50-letiya Oktyabrya St., Ufa, 450001, Russia

    Ramil R. Zaripov

Authors
  1. Shamil M. Salikhov
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  2. Ramil R. Zaripov
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  3. Lyaisan R. Latypova
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  4. Ildus B. Abdrakhmanov
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Corresponding author

Correspondence to Shamil M. Salikhov.

Additional information

Supplementary information file containing 1Н and 13С NMR spectra, as well as two-dimensional 1Н–13С and 1Н–15N HMBC, 1Н–13С HSQC, and COSY spectra of all synthesized compounds, is available from the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 660–664

* For Communication 1, see 1.

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Salikhov, S.M., Zaripov, R.R., Latypova, L.R. et al. Intramolecular heterocyclization of o-(1-cycloalkenyl)anilines 2*. Synthesis of new 4Н-3,1-benzoxazine and 4Н-3,1-benzothiazine 2-amino derivatives. Chem Heterocycl Comp 55, 660–664 (2019). https://doi.org/10.1007/s10593-019-02513-6

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  • DOI: https://doi.org/10.1007/s10593-019-02513-6

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