82414-33-3

Upstream product

• 59-48-3 2-oxoindole 
• 541-41-3 chloroformic acid ethyl ester 
• 91-56-5 indole-2,3-dione 
• 301700-12-9 2-ethoxycarbonyloxy-indole-1-carboxylic acid ethyl ester 
• 82414-30-0 C₂₅H₂₁N₃O₄ 

Downstream Products

• 1579957-13-3 C₃₁H₂₇NO₇ 
• 1309883-39-3 ethyl (2S,6S)-2,6-bis(2-bromophenyl)-2',4-dioxospiro[cyclohexane-1,3'-indoline]-1'-carboxylate 
• 1309883-38-2 ethyl (2R,6R)-2,6-bis(3-bromophenyl)-2',4-dioxospiro[cyclohexane-1,3'-indoline]-1'-carboxylate 
• 1309883-36-0 ethyl (2R,6R)-2',4-dioxo-2,6-diphenylspiro[cyclohexane-1,3'-indoline]-1'-carboxylate 
• 1309883-43-9 ethyl (2S,6S)-2,6-bis(2-chlorophenyl)-2',4-dioxospiro[cyclohexane-1,3'-indoline]-1'-carboxylate 
• 1309883-49-5 ethyl (2R,6R)-2,6-bis(4-nitrophenyl)-2',4-dioxospiro[cyclohexane-1,3'-indoline]-1'-carboxylate 
• 1309883-46-2 ethyl (2R,6R)-2',4-dioxo-2,6-di-p-tolylspiro[cyclohexane-1,3'-indoline]-1'-carboxylate 
• 1309883-44-0 ethyl (2R,6R)-2,6-bis(4-fluorophenyl)-2',4-dioxospiro[cyclohexane-1,3'-indoline]-1'-carboxylate 
• 1309883-48-4 ethyl (2R,6R)-2',4-dioxo-2,6-bis(4-(trifluoromethyl)phenyl)spiro[cyclohexane-1,3'-indoline]-1'-carboxylate 

Relevant academic research and scientific papers

Enantioselective C2-Alkylation of Indoles through a Redox-Relay Heck Reaction of 2-Indole Triflates

A palladium-catalyzed enantioselective redox-relay Heck reaction of 2-indole triflates and disubstituted alkenes is reported. This process combines readily available indole triflates with a variety of alkenes to afford a range of indole derivatives bearing a stereocenter adjacent to C2. Enantioselectivity is achieved through use of a simple pyridine-oxazoline ligand. Tuning the electronics of the indole, through judicious choice of N-protecting group, is required to ensure selective β-hydride elimination away from the indole core. Utility of this method is highlighted in a modular formal synthesis of an S1P1 agonist precursor developed by Merck.

Regioselective synthesis of heteroaryl triflones by LDA (lithium diisopropylamide)-mediated anionic thia-Fries rearrangement

Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

2-Trifluoromethanesulfonyloxyindole-1-carboxylic acid ethyl ester: A practical intermediate for the synthesis of 2-carbosubstituted indoles

Ready accessible 2-trifluoromethanesulfonyloxyindole-1-carboxylic acid ethyl ester undergoes palladium-catalyzed coupling reactions with different partners giving rise to 2-aryl, heteroaryl, vinyl, allyl, and alkynyl indoles in good to excellent yields. G

New routes to oxindole derivatives

A new, practical synthesis of the antirheumatic oxindole derivative, tenidap, has been elaborated. The new approach has initiated studies on the mechanism of the acylation reactions of oxindoles. Methods have been developed for the synthesis of 1-[alkoxy(or aryloxy)carbonyl]- and 1,3-di[alkoxy(or aryloxy)carbonyl]oxindoles starting from oxindoles. The route designed for tenidap has provided a facile access to several analogues, too. On another front, new reaction conditions are described, which turn Wenkert's synthesis of 3-alkyloxindoles (by Raney nickel induced alkylation of oxindoles with alcohols) into a highly efficient synthetic tool. The method has been extended to the synthesis of 3-alkyloxindoles from isatins and to the preparation of 3-(ω-hydroxyalkyl)oxindoles from oxindoles and isatins. Springer-Verlag 2004.

Synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles

Two protocols have been developed for the synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles starting from the corresponding N,O-diacyl derivatives obtained by treatment of 2-oxindoles with chloroformic acid esters and triethylamine. Th

SELECTIVITY IN CYCLOADDITIONS-IX CYCLOADDITIONS OF NITRILE OXIDES TO INDOLES. REACTIVITY AND REGIOCHEMISTRY

Cycloadditions of benzonitrile oxide and mesitonitrile oxide to N-methylindole and indole yield the acid sensitive cycloadducts 1 a-d with high regioselectivity.With N-carbethoxyindole the stable cycloadducts 1 e,f and minor amounts of the regioisomeric 2 e,f are isolated.The electron withdrawing substituent reduces both the regioselectivity and the reactivity of the cycloadditions.Frontier orbital considerations, based on MINDO/3 calculations, allow elucidation of the observed changes in reactivity and regiochemistry.