Synthesis of some heterocyclic aminoimidazoazarenes

Abstract

The reaction mechanism of the synthesis of 2-amino-3,4-dimethylimidazo(4,5-f)-quinoline and 2-amino-3,4,8-trimethylimidazo(4,5-f)quinoxaline as compounds of the new class of mutagenic heterocyclic amines, amino-imidazoazarenes, in the reaction between aldoses, amino acids and creatinine, has been studied. The reaction involves two reaction steps: (a) the initial step and (b) the steady-state reaction step. The initial step depends on the existence and kinetics of the Maillard and Strecker reactions and pyridine and pyrazine free radical formations. Stabilization of the formed free radicals occurs in the steady-state step, giving pyridine and pyrazine derivatives. These compounds reacted with creatinine and formed amino-imidazoazarenes. The proposed reaction mechanism of the formation of the amino-imidazoazarenes has been studied by Electron Spin Resonance (ESR), 1H Nuclear Magnetic Resonance (1H NMR) spectroscopy and Mass spectrometry (MS). © 1992.