Facile and efficient aromatization of 1,4-dihydropyridines with M(NO3)2.XH2O, TNCB, TBAP and HMTAI and preparation of deuterium labeled dehydronifedipine from nifedipine-d3

Bioorg Med Chem Lett. 2010 Jun 15;20(12):3664-8. doi: 10.1016/j.bmcl.2010.04.096. Epub 2010 Apr 24.

Abstract

The easy and efficient aromatization of various 1,4-dihydropyridines was investigated using various metal nitrates, trinitratocerium(IV) bromate (TNCB), and tetrabutyl ammonium periodate (TBAP) as oxidant in acetic acid at 100 degrees C, as well as hexamethylenetetramine-iodine (HMTAI) reflux in methanol. The efficient conversion of nifedipine-d(3) to dehydronifedipine-d(3) as an internal standard can be used in the measurement of nifedipine concentration in a body.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calcium Channel Blockers / chemistry
  • Deuterium / chemistry*
  • Dihydropyridines / chemistry*
  • Humans
  • Metals / chemistry
  • Methenamine / chemistry
  • Nifedipine / analogs & derivatives*
  • Nifedipine / analysis*
  • Nifedipine / chemical synthesis
  • Nifedipine / chemistry*
  • Nifedipine / standards
  • Nitrates / chemistry
  • Quaternary Ammonium Compounds / chemistry
  • Radiopharmaceuticals / chemical synthesis
  • Vasodilator Agents / chemistry

Substances

  • Calcium Channel Blockers
  • Dihydropyridines
  • Metals
  • Nitrates
  • Quaternary Ammonium Compounds
  • Radiopharmaceuticals
  • Vasodilator Agents
  • dehydronifedipine
  • 1,4-dihydropyridine
  • Deuterium
  • tetrabutylammonium
  • Nifedipine
  • Methenamine