Beilstein J. Org. Chem.2014,10, 692–700, doi:10.3762/bjoc.10.62
-700032, India 10.3762/bjoc.10.62 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
[3,2-h]quinoliniums; phenanthroliums; pyrrolo[1,2-a]phenanthrolines; pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines; Introduction
The chemistry of the 1,3-dipolar cycloaddition has always been a fascinating undertaking especially when azomethine ylides are involved as the key component
after an extensive screening, we found copper(II) chloride–phenanthroline as the best catalytic pair for this purpose. Herein we wish to present the results of our recent synthetic efforts to synthesize a series of unique pentacyclic pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines using
PDF
Graphical Abstract
Scheme 1:
Preparation of maleimide dipolarophiles 4a–c.