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

Rupankar Paira; Tarique Anwar; Maitreyee Banerjee; Yogesh P Bharitkar; Shyamal Mondal; Sandip Kundu; Abhijit Hazra; Prakas R Maulik; Nirup B Mondal

doi:10.3762/bjoc.10.62

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

Beilstein J Org Chem. 2014 Mar 20:10:692-700. doi: 10.3762/bjoc.10.62. eCollection 2014.

Authors

Rupankar Paira¹, Tarique Anwar¹, Maitreyee Banerjee¹, Yogesh P Bharitkar¹, Shyamal Mondal¹, Sandip Kundu¹, Abhijit Hazra¹, Prakas R Maulik¹, Nirup B Mondal¹

Affiliation

¹ Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India.

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