Unknown

Dataset Information

0

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.

SUBMITTER: Filatov V 

PROVIDER: S-EPMC9051608 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Synthesis of 1,3-diaryl-spiro[azetidine-2,3'-indoline]-2',4-diones <i>via</i> the Staudinger reaction: <i>cis</i>- or <i>trans</i>-diastereoselectivity with different addition modes.

Filatov Vadim V   Kukushkin Maksim M   Kuznetsova Juliana J   Skvortsov Dmitry D   Tafeenko Viktor V   Zyk Nikolay N   Majouga Alexander A   Beloglazkina Elena E  

RSC advances 20200406 24

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-s  ...[more]

Similar Datasets

Unknown 1',3',3'-Trimethyl-2,3-diphenyl-2,3-di-hydro-isoxazole-5(4H)-spiro-2'-indoline.
| S-EPMC2968171 | biostudies-literature
Unknown Discovery of 3,3'-Spiro[Azetidine]-2-oxo-indoline Derivatives as Fusion Inhibitors for Treatment of RSV Infection.
| S-EPMC5807868 | biostudies-literature
Unknown Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines.
| S-EPMC3869290 | biostudies-literature
Unknown 2'-Eth-oxy-1,3,3-trimethyl-spiro-[indoline-2,3'-3H-naphtho-[2,1-b][1,4]oxazine].
| S-EPMC3006916 | biostudies-literature
Unknown Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones and novel ring contraction and fusion reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] into 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones.
| S-EPMC3628778 | biostudies-literature
Unknown Multi-Component Syntheses of Spiro[furan-2,3'-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts.
| S-EPMC10976190 | biostudies-literature
Unknown Synthesis and Docking Studies of Novel Spiro[5,8-methanoquinazoline-2,3'-indoline]-2',4-dione Derivatives.
| S-EPMC11547464 | biostudies-literature
Unknown Methyl 4-(4-bromo-anilino)-2',5-dioxo-5H-spiro-[furan-2,3'-indoline]-3-carboxyl-ate.
| S-EPMC3998355 | biostudies-literature
Unknown Synthesis of furan-2-ones and spiro[furan-2,3'-indoline] derivatives using polyether sulfone sulfamic acid catalysis.
| S-EPMC11522323 | biostudies-literature
Unknown (1S,3R)-3-Isobutyl-2,3-dihydro-spiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione methanol monosolvate.
| S-EPMC3414972 | biostudies-literature