Reductive Cleavage of 4′<i>H</i>-Spiro[indole-3,5′-isoxazoles] En Route to 2-(1<i>H</i>-Indol-3-yl)acetamides with Anticancer Activities
А. В. Аксенов, Nikita K. Kirilov, Nikolai A. Arutiunov, Дмитрий А. Аксенов, Iliya K. Kuzminov, Nicolai A. Aksenov, Danielle N. Turner, Snezna Rogelj, Alexander Kornienko, Michael Rubin
Abstract
Unusual cascade transformation involving ring opening and 1,2-alkyl shift was observed upon the reduction of 4′H-spiro[indole-3,5′-isoxazoles] or 2-(3-oxoindolin-2-yl)acetonitriles with sodium borohydride. This reaction allowed for expeditious and highly efficient preparation of 2-(1H-Indol-3-yl)acetamides with antiproliferative properties.
Topics & Concepts
Indole testAcetonitrilesSodium borohydrideChemistryCleavage (geology)Ring (chemistry)StereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryBiologyCatalysisPaleontologyAcetonitrileFracture (geology)Synthesis and Biological EvaluationSynthesis and Reactions of Organic CompoundsChemical Reaction Mechanisms