Utility of 6-methylchromone-3- carbonitrile in heterocyclic synthesis

Abstract

Chromone derivatives represent an important class of oxygen containing heterocyclic compounds, which are widely spread in plants1-3 and exhibit wide range of biological and pharmacological activities including anti-inflammatory,4 anti-HIV,5 anticancer,6 antibacterial,7 antimalarial,8 antitumor,9 as well as treatment of Alzheimer’s disease.10 The presence of the electron-withdrawing cyano group at the position 3 of the chromone system changes crucially the chemical reactivity of the γ-pyrone ring with respect to nucleophiles, and provides a broad synthetic potential of chromone-3-carbonitriles.11-14 They have the ability to undergo a nucleophilic 1,4-attack followed by additional transformations related to γ-pyrone ring opening and heterocyclizations at the C-4 atom and/or at the cyano group.15-19 Herein, we aimed to study the chemical transformations of 6-methylchromone-3-carbonitrile (1) towards some nitrogen nucleophiles.