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[4+2]-Cycloaddition of 1,1,3,3-tetramethylguanidine and o-quinone methides: synthesis of arene-fused 2-dimethylamino-4H-1,3-oxazines

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Abstract

A method for producing substituted 4H-1,3-benzoxazines and their fused derivatives bearing N,N-dimethylamino moiety in the position 2 of 4H-1,3-oxazine ring from phenolic and naphtholic Mannich bases, their iodomethylates or salicylic alcohols, and 1,1,3,3-tetramethylguanidine has been developed. This reaction is supposed to proceed via the generation of o-quinone methides followed by [4+2]-cycloaddition and elimination of dimethylamine.

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvargeyskaya ul., 443100, Samara, Russian Federation

    V. A. Osyanin, D. V. Osipov, P. E. Krasnikov & V. A. Shiryaev

Authors
  1. V. A. Osyanin
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  2. D. V. Osipov
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  3. P. E. Krasnikov
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  4. V. A. Shiryaev
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Corresponding author

Correspondence to V. A. Osyanin.

Additional information

The study was financially supported by the the Russian Science Foundation (Project No. 22-13-00253) with the use of the equipment of the Multi-Access Center “Investigation of the Physicochemical Properties of Substances and Materials” of the SSTU.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Based on the materials of the VI North Caucasus Symposium on Organic Chemistry NCOCS-2022 (April 18–22, 2022, Stavropol, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2451–2459, November, 2022.

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Osyanin, V.A., Osipov, D.V., Krasnikov, P.E. et al. [4+2]-Cycloaddition of 1,1,3,3-tetramethylguanidine and o-quinone methides: synthesis of arene-fused 2-dimethylamino-4H-1,3-oxazines. Russ Chem Bull 71, 2451–2459 (2022). https://doi.org/10.1007/s11172-022-3673-1

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