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Synthesis of new pyrido[3,2-b][1,4]benzoxazines and -benzothiazines

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Abstract

New pyrido[3,2-b][1,4]benzoxazines and pyrido[3,2-b][1,4]benzothiazines were synthesized by the base-mediated reactions of substituted 2-chloro-3-nitropyridines with o-amino(thio)phenols. The reactions involve a sequential nucleophilic substitution of the chlorine atom and the nitro group affected by either O,N- or S,N-binucleophile. In the case of aminothiophenols, the reaction proceeded via substitution of the chlorine atom followed by the Smiles rearrangement, and an intramolecular substitution of the nitro group by S-nucleophile.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. M. Starosotnikov, V. V. Ivanova, T. A. Klimova, N. G. Kolotyrkina & M. A. Bastrakov

  2. Dmitry Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    V. V. Ivanova

Authors
  1. A. M. Starosotnikov
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  2. V. V. Ivanova
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  3. T. A. Klimova
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  4. N. G. Kolotyrkina
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  5. M. A. Bastrakov
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Corresponding author

Correspondence to A. M. Starosotnikov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 126–130, January, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Starosotnikov, A.M., Ivanova, V.V., Klimova, T.A. et al. Synthesis of new pyrido[3,2-b][1,4]benzoxazines and -benzothiazines. Russ Chem Bull 71, 126–130 (2022). https://doi.org/10.1007/s11172-022-3385-6

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  • DOI: https://doi.org/10.1007/s11172-022-3385-6

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