Application of Vitreoscilla Hemoglobin as a Green and Efficient Biocatalyst for the Synthesis of Benzoxazoles in Water

Chembiochem. 2024 Jan 2;25(1):e202300609. doi: 10.1002/cbic.202300609. Epub 2023 Nov 7.

Abstract

We report an efficient and eco-friendly method for the Vitreoscilla hemoglobin (VHb)-catalyzed synthesis of benzoxazoles in water at room temperature. tert-Butyl hydroperoxide and 2,2,6,6-tetramethyl-1-piperidinyloxy were used as oxidant and radical scavenger, respectively. A total of 27 functionally diverse benzoxazoles were prepared in moderate to high yields (62 %-94 %) by the annulation reaction of phenols with amines in the presence of VHb in 1 h. Thus, this method is highly viable for practical applications. This work broadens the application of hemoglobin to organic synthesis.

Keywords: Vitreoscilla hemoglobin; annulation reaction; benzoxazoles; biocatalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Proteins
  • Benzoxazoles*
  • Truncated Hemoglobins
  • Water*

Substances

  • hemoglobin protein, Vitreoscilla
  • Benzoxazoles
  • Water
  • Truncated Hemoglobins
  • Bacterial Proteins