Issue 24, 2020

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

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
14 3月 2020
Accepted
30 3月 2020
First published
06 4月 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 14122-14133

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

V. Filatov, M. Kukushkin, J. Kuznetsova, D. Skvortsov, V. Tafeenko, N. Zyk, A. Majouga and E. Beloglazkina, RSC Adv., 2020, 10, 14122 DOI: 10.1039/D0RA02374D

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