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Azolyl Derivatives of Nitrohalobutadienes: V. A New Route to Functionally Substituted Benzazetines

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Abstract

Heating of 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4,4-trichloro-1,3-butadienes and 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4-dichloro-4-bromo-1,3-butadienes (R = BuO, EtO, MeO, Me; azolyl = 1-benzotriazolyl, 3,5-dimethyl-1-pyrazolyl, and 1,2,4-triazol-1-yl) in methanol or acetic acid gave the corresponding 2-(1-nitrotrihalopropenylidene)-4-R-benzazetines. The latter reacted with amines, sodium alkoxides, and sodium thiolates, affording salts of the aci-nitro form. The reactions with benzoyl chloride and chloroacetyl chloride in the presence of pyridine led to formation of mixed anhydrides.

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Authors and Affiliations

  1. National Academy of Sciences of Belarus, Institute of Physical Organic Chemistry, ul. Surganova 13, Minsk, 220072, Belarus

    V. I. Potkin, V. A. Zapol'skii, V. A. Knizhnikov, R. V. Kaberdin, A. A. Yanuchok & S. K. Petkevich

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  1. V. I. Potkin
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  2. V. A. Zapol'skii
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  3. V. A. Knizhnikov
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  4. R. V. Kaberdin
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  5. A. A. Yanuchok
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  6. S. K. Petkevich
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Potkin, V.I., Zapol'skii, V.A., Knizhnikov, V.A. et al. Azolyl Derivatives of Nitrohalobutadienes: V. A New Route to Functionally Substituted Benzazetines. Russian Journal of Organic Chemistry 37, 689–694 (2001). https://doi.org/10.1023/A:1012451901837

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