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
procedure to synthesize pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines 10a–h, pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]phenanthrolines 14a–c, and pyrrolo[1,2-a]phenanthrolines 14d–g: A mixture of 3.3 mmol furo[3,2-h]quinolinium derivatives 9a–d/phenanthroliniums 12a,b and 3.3 mmol N-phenylmalimide derivatives 4a–d
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Graphical Abstract
Scheme 1:
Preparation of maleimide dipolarophiles 4a–c.