Laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the synthesis of pyrimidobenzothiazole derivatives

J Org Chem. 2013 Aug 16;78(16):7986-8003. doi: 10.1021/jo401193e. Epub 2013 Jul 26.

Abstract

The laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles using aerial O2 as the oxidant delivers new pyrimidobenzothiazole derivatives. The complete structure elucidation of the ring-proton deficient heterocyclic products and the unambiguous determination of the regioselectivity of the reactions have been achieved by extended NMR spectroscopic methods including HSQMBC, super long-range HMBC, and (15)N measurements.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzothiazoles / chemistry
  • Benzothiazoles / metabolism*
  • Catalysis
  • Catechols / chemistry
  • Catechols / metabolism*
  • Laccase / chemistry
  • Laccase / metabolism*
  • Molecular Structure
  • Nitriles / chemistry
  • Nitriles / metabolism*
  • Pyrimidines / chemistry
  • Pyrimidines / metabolism*
  • Quantum Theory

Substances

  • 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitrile
  • Benzothiazoles
  • Catechols
  • Nitriles
  • Pyrimidines
  • Laccase