NMR characterization of new 10-membered-ring macrolactones and dihydrobenzophenazine-5-one, oxidized derivatives of benzo[a]phenazines

Magn Reson Chem. 2004 Jul;42(7):663-5. doi: 10.1002/mrc.1395.

Abstract

Peroxidation of the phenazine of beta-lapachone using m-ClC6H4CO3H-CH2Cl2 furnished a macrolactone with a rigid 10-membered ring, and the corresponding N-oxide, along with a dihydrobenzophenazine-5-one. All of the new compounds were fully characterized by spectroscopic methods, with the unambiguous assignment of the hydrogens and carbon NMR signals for the N-oxide, with the aid of 2-D NMR, mainly COSY, HMQC, HSQC and HMBC. For the other two compounds some signals could not be assigned owing to their own intrinsic features.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Isotopes
  • China
  • Lactones / analysis
  • Lactones / chemistry*
  • Magnetic Resonance Spectroscopy / methods*
  • Magnetic Resonance Spectroscopy / standards*
  • Models, Molecular*
  • Molecular Conformation
  • Oxidation-Reduction
  • Phenazines / analysis
  • Phenazines / chemistry*
  • Protons
  • Reference Standards
  • Stereoisomerism

Substances

  • Carbon Isotopes
  • Lactones
  • Phenazines
  • Protons