1185774-33-7

Upstream product

• 59-48-3 2-oxoindole 
• 6630-33-7 ortho-bromobenzaldehyde 
• 391614-10-1 3-(2-bromobenzylidene)oxindole 

Downstream Products

• 1185774-47-3 (S)-diisopropyl 1-(3-(2-bromobenzyl)-2-oxoindolin-3-yl)hydrazine-1,2-dicarboxylate 
• 1398681-60-1 3-bromo-3-(2-bromobenzyl)indolin-2-one 
• 1398681-30-5 benzaldehyde O-3-(2-bromobenzyl)-2-oxoindolin-3-yl oxime 

Relevant academic research and scientific papers

Chiral N,N′-Dioxide/Scandium(III)-Catalyzed Asymmetric Alkylation of N-Unprotected 3-Substituted Oxindoles

An efficient enantioselective alkylation of N-unprotected 3-substituted oxindoles was realized by using a chiral N,N′-dioxide/scandium(III) complex as the catalyst. A wide range of 3,3-dialkyl substituted oxindoles with quaternary stereocenters were obtained in high yields and ee values (up to 98% yield and 99% ee). (Figure presented.).

Transition-metal-free Chemoselective Oxidative C?C Coupling of the sp3 C?H Bond of Oxindoles with Arenes and Addition to Alkene: Synthesis of 3-Aryl Oxindoles, and Benzofuro- and Indoloindoles

A transition-metal (TM)-free and halogen-free NaOtBu-mediated oxidative cross-coupling between the sp3 C?H bond of oxindoles and sp2 C?H bond of nitroarenes has been developed to access 3-aryl substituted and 3,3-aryldisubstituted oxindoles in DMSO at room temperature in a short time. Interestingly, the sp3 C?H bond of oxindoles could also react with styrene under TM-free conditions for the practical synthesis of quaternary 3,3-disubstituted oxindoles. The synthesized 3-oxindoles have also been further transformed into advanced heterocycles, that is, benzofuroindoles, indoloindoles, and substituted indoles. Mechanistic experiments of the reaction suggests the formation of an anion intermediate from the sp3 C?H bond of oxindole by tert-butoxide base in DMSO. The addition of nitrobenzene to the in-situ generated carbanion leads to the 3-(nitrophenyl)oxindolyl carbanion in DMSO which is subsequently oxidized to 3-(nitro-aryl) oxindole by DMSO.

Organocatalytic enantioselective stereoablative hydroxylation of 3-halooxindoles: An effective method for the construction of enantioenriched 3-substituted 3-hydroxy-2-oxindoles

3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme).

Highly enantioselective and organocatalytic α-amination of 2-Oxindoles

Figur Presented An effective method for the asymmetric synthesis of 3-amino-2-oxindoles was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of N-unprotected 2-oxindoles with azodicarboxylate catalyzed by commercial biscinchona alkaloids in good to excellent yields with high enantioselectivities.