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

• Published in: Beilstein journal of organic chemistry Vol. 10; no. 1; pp. 692 - 700
• Main Authors: Paira, Rupankar, Anwar, Tarique, Banerjee, Maitreyee, Bharitkar, Yogesh P, Mondal, Shyamal, Kundu, Sandip, Hazra, Abhijit, Maulik, Prakas R, Mondal, Nirup B
• Format: Journal Article
• Language: English
• Published: Germany Beilstein-Institut 20.03.2014
• Subjects: 1,3-dipolar cycloaddition; Chemistry; copper(II) chloride–phenanthroline; Full Research Paper; furo[3,2-h]quinoliniums; phenanthroliums; pyrrolo[1,2-a]phenanthrolines; pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines; phenanthroliums; furo[3,2-h]quinoliniums; copper(II) chloride–phenanthroline; pyrrolo[1,2-a]phenanthrolines; pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines; 1,3-dipolar cycloaddition
• ISSN: 1860-5397; 1860-5397
• DOI: 10.3762/bjoc.10.62

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.