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Intramolecular Heterocyclization of o-(1-Cycloalkenyl)anilines: III. Synthesis of Optically Active 4H-3,1-Benzoxazines Based on α-Amino Acids

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Abstract

A new approach has been proposed to the synthesis of optically active 4H-3,1-benzoxazine derivatives based on α-amino acids. The target products have been obtained by reaction of o-(cyclopent-1-en-1-yl)aniline with N-Boc-protected amino acids, followed by removal of the protecting group and heterocyclization by the action of dry hydrogen chloride in methylene chloride.

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ACKNOWLEDGMENTS

Chemical analyses were carried out using the facilities of the Chemistry joint center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment nos. AAAA-A20-120012090029-0, AAAA-A19- 119011790021-4.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    Sh. M. Salikhov & I. B. Abdrakhmanov

  2. Bashkir State Agrarian University, 450001, Ufa, Russia

    R. R. Zaripov

Authors
  1. Sh. M. Salikhov
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  2. R. R. Zaripov
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  3. I. B. Abdrakhmanov
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Correspondence to Sh. M. Salikhov or R. R. Zaripov.

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The authors declare no conflict of interest.

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For communication II, see [1].

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Salikhov, S.M., Zaripov, R.R. & Abdrakhmanov, I.B. Intramolecular Heterocyclization of o-(1-Cycloalkenyl)anilines: III. Synthesis of Optically Active 4H-3,1-Benzoxazines Based on α-Amino Acids. Russ J Org Chem 56, 1613–1621 (2020). https://doi.org/10.1134/S1070428020090183

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