Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions

Abstract

A new series of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in situ from the parent furo[3,2-h]quinoliniums/phenanthroliums, in presence of a copper(II) chloride–phenanthroline catalytic system. The methodology combines general applicability with high yields.

Keywords

• copper(II) chloride–phenanthroline
• 1,3-dipolar cycloaddition
• furo[3,2-h]quinoliniums
• phenanthroliums
• pyrrolo[1,2-a]phenanthrolines
• pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines