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We report regioselective intramolecular direct C-3 and C-2 arylations of the indole rings of N-(o-bromophenyl)-3-indolecarboxamides for diastereospecific production of spiro-indoline-3,3′-oxindoles and 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones, respectively, under different reaction conditions and possibly involving two different pathways.

Graphical abstract: Pd-catalyzed regioselective intramolecular direct arylation of 3-indolecarboxamides: access to spiro-indoline-3,3′-oxindoles and 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones

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