Synthesis of Quinone Derivatives of Benzannelated Heterocycles with Bridgehead Nitrogen
Р. С. Бегунов, А. А. Соколов, С. И. Филимонов
Abstract
Abstract A facile synthesis of para-quinones derived from fused benzimidazoles with a bridgehead nitrogen atom was developed. The heterocyclic quinone core formed as a result of reductive cyclization of ortho-nitroarenes containing alicyclic and aromatic azaheterocycles. Functionalization of 1,2,3,4-tetrahydro- and pyrido[1,2-a]benzimidazoles via SEAr, condensation, and reduction reactions allowed synthesis of amino derivatives which were oxidized with KNO3 in H2SO4 to obtain novel heterocyclic quinones.
Topics & Concepts
ChemistryAlicyclic compoundQuinoneNitrogen atomNitrogenCondensationOrganic chemistryCombinatorial chemistryAnnulationRing (chemistry)CatalysisPhysicsThermodynamicsBioactive Compounds and Antitumor AgentsSynthesis and biological activitySynthesis and Reactions of Organic Compounds