Nikolai A. Arutiunov, Anna M. Zatsepilina, Anna A. Aksenova, Nicolai A. Aksenov, Dmitrii A. Aksenov, Alexander V. Leontiev and Alexander V. Aksenov*,
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One-Pot Synthesis of N-Fused Quinolone-4 Tetracyclic Scaffolds from 2,2-Disubstituted Indolin-3-ones
A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly of complex (dihydro)indolo[1,2-a]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation of 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones to the corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. The latter can either be isolated with good yields (75–96%) or, in the case of o-nitroacetophenone, used in situ for further base-assisted intramolecular SNAr cyclization resulting in indoxyl-fused quinolone-4 hybrids (up to 95%).
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