Synthesis of 1, 3-diaryl-spiro[azetidine-2, 3′-indoline]-2′, 4-diones via the Staudinger reaction: cis- or trans-diastereoselectivity with different addition modes. Issue 24 (6th April 2020)

• Record Type: Journal Article
• Authors: Filatov, Vadim; Kukushkin, Maksim; Kuznetsova, Juliana; Skvortsov, Dmitry; Tafeenko, Viktor; Zyk, Nikolay; Majouga, Alexander; Beloglazkina, Elena
• Is Part Of: RSC advances. Volume 10:Issue 24(2020)
• Page Start: 14122
• Page End: 14133
• Publication Date: 2020-04-06
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0ra02374d
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Two experimental techniques of the ketene–imine Staudinger reaction allowed different diastereomers of spiro-indolinone-β-lactams to be obtained. Abstract : A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2, 3′-indoline]-2′, 4-diones was developed based on Staudinger ketene–imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2, 3′-indoline]-2′, 4-diones were synthesized using this method. For comparison, the same compounds were obtained using a known technique, where ketene is generated from pre-synthesized acyl chloride. It was shown that the use of oxalyl chloride for ketene generation in the one-pot reaction at room temperature allows for the reversal of the diastereoselectivity of spiro-lactam formation, unlike previously described procedures.