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2-Aryl-4H-3,1-benzoxazin-4-ones alcoholysis

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 2-(2-tosylaminophenyl)-4H-3,1-benzoxazine-4-one with alcohols in pyridine gives tosylanthraniloylanthranilic acid esters. The synthesized compounds luminesce in the crystalline state and in solutions at room temperature. The anomalously high Stokesian shift characteristic for this series of compounds is due to intramolecular hydrogen bonding with the participation of the tosylamino group. Interaction of polar solvents and irradiation with UV light lead to cleavage of the hydrogen bond, and as a consequence, to a decrease in the Stokesian shift.

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Authors
  1. B. M. Bolotin
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  2. N. I. Kunavin
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  3. L. S. Zeryukina
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  4. R. U. Safina
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 760–763, June, 1974.

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Bolotin, B.M., Kunavin, N.I., Zeryukina, L.S. et al. 2-Aryl-4H-3,1-benzoxazin-4-ones alcoholysis. Chem Heterocycl Compd 10, 658–661 (1974). https://doi.org/10.1007/BF00480917

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  • DOI: https://doi.org/10.1007/BF00480917

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