Reductive Cleavage of 4′H-Spiro[indole-3,5′-isoxazoles] En Route to 2-(1H-Indol-3-yl)acetamides with Anticancer Activities

• DOI: 10.1021/acs.joc.2c01627
• Publication Date: 2022-10-19T15:07:00Z
• Authors: Alexander V. Aksenov; Nikita K. Kirilov; Nikolai A. Arutiunov; Dmitrii A. Aksenov; Iliya K. Kuzminov; Nicolai A. Aksenov; Danielle N. Turner; Snezna Rogelj; Alexander Kornienko; Michael Rubin
• Keywords: Acetonitriles; Sodium borohydride; Cleavage (geology)

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 highly efficient preparation 2-(1H-Indol-3-yl)acetamides antiproliferative properties.