Synthesis of Quinolino[3′,4′:4,5]pyrrolo[1,2‐f]phenanthridines by Regioselective Sonogashira Reaction Followed by Domino C–N Coupling/Hydroamination/C–H Arylation

An effective and atom‐economic synthesis of quinolino[3′,4′:4,5]pyrrolo[1,2‐f]phenanthridines has been developed. The protocol involves a site‐selective Sonogashira reaction of 3,4‐dihaloquinoline, followed by a domino C–N coupling/hydroamination/C–H arylation reaction. Quinolino[3′,4′:4,5]pyrrolo[1...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-07, Vol.2017 (26), p.3865-3873
Main Authors: Pham, Ngo Nghia, Salman, Ghazwan Ali, Ponce, Marian Blanco, Dang, Tuan Thanh, Spannenberg, Anke, Ehlers, Peter, Langer, Peter
Format: Article
Language:English
Subjects:
Coupling
Cyclization
Domino reactions
Heterocycles
Heterocyclic compounds
Homogeneous catalysis
Palladium
Regioselectivity
Synthesis
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Summary:An effective and atom‐economic synthesis of quinolino[3′,4′:4,5]pyrrolo[1,2‐f]phenanthridines has been developed. The protocol involves a site‐selective Sonogashira reaction of 3,4‐dihaloquinoline, followed by a domino C–N coupling/hydroamination/C–H arylation reaction. Quinolino[3′,4′:4,5]pyrrolo[1,2‐f]phenanthridines represent a hitherto unknown class of heterocyclic compounds. A convenient synthesis of quinolino[3′,4′:4,5]pyrrolo[1,2‐f]phenanthridines from alkynylated quinolines is described. The process is mediated by a single palladium catalyst in one step, involving a Buchwald–Hartwig amination followed by a hydroamination and an intramolecular C–H activation step.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700371