Synthesis of Indolo[2,3-<i>c</i>]quinolin-6(7<i>H</i>)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C–H Arylation
Tímea Szabó, Marcell Papp, Dóra R. Németh, András Dancsó, Balázs Volk, Mátyás Milen
Abstract
The synthesis of variously substituted indolo[2,3-c]quinolin-6(7H)-ones was developed via Pd-catalyzed intramolecular C–H arylation. This method highlights a strategy for preparing indoloquinoline precursors bearing versatile functional groups and provides a new approach for the synthesis of antimalarial isoneocryptolepine analogues. The plausible ring closure mechanism was examined with quantum chemical calculations, where a trigonal bipyramidal concerted metalation–deprotonation transition state is presumable.
Topics & Concepts
ChemistryIntramolecular forceMetalationDeprotonationRing (chemistry)StereochemistryCatalysisMedicinal chemistryCombinatorial chemistryOrganic chemistryIonSynthesis and bioactivity of alkaloidsSynthesis and pharmacology of benzodiazepine derivativesSynthesis and Reactivity of Heterocycles