Skip to main content
placeholder image

Structural Elucidation and Independent Synthesis of the Radical-Radical Coupling Products of 3-Hydroxyanthranilic Acid with Tyrosine and Phenols

Journal Article


Abstract


  • The autoxidation of 3-hydroxyanthranilic acid (30HA) in the presence of tyrosine, p-cresol, or p-ethylphenol gives dibenzo[b,d]pyran-6-one products that arise from the coupling of the radical of 30HA with that derived from the substituted phenol. As a proof of the structure of these adducts, they have been independently synthesized by employing a palladium(0)-catalyzed coupling of appropriately functionalized aryl boronic acids with methyl 6-bromo-3-methoxy-2-nitrobenzoate. © 1990, American Chemical Society. All rights reserved.

Publication Date


  • 1990

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1990). Structural Elucidation and Independent Synthesis of the Radical-Radical Coupling Products of 3-Hydroxyanthranilic Acid with Tyrosine and Phenols. Journal of Organic Chemistry, 55(15), 4581-4585. doi:10.1021/jo00302a022

Scopus Eid


  • 2-s2.0-0012045739

Web Of Science Accession Number


Start Page


  • 4581

End Page


  • 4585

Volume


  • 55

Issue


  • 15

Abstract


  • The autoxidation of 3-hydroxyanthranilic acid (30HA) in the presence of tyrosine, p-cresol, or p-ethylphenol gives dibenzo[b,d]pyran-6-one products that arise from the coupling of the radical of 30HA with that derived from the substituted phenol. As a proof of the structure of these adducts, they have been independently synthesized by employing a palladium(0)-catalyzed coupling of appropriately functionalized aryl boronic acids with methyl 6-bromo-3-methoxy-2-nitrobenzoate. © 1990, American Chemical Society. All rights reserved.

Publication Date


  • 1990

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1990). Structural Elucidation and Independent Synthesis of the Radical-Radical Coupling Products of 3-Hydroxyanthranilic Acid with Tyrosine and Phenols. Journal of Organic Chemistry, 55(15), 4581-4585. doi:10.1021/jo00302a022

Scopus Eid


  • 2-s2.0-0012045739

Web Of Science Accession Number


Start Page


  • 4581

End Page


  • 4585

Volume


  • 55

Issue


  • 15