1922-79-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 1671, 1995 DOI: 10.1016/0040-4039(95)00126-W

Upstream product

• 39033-45-9 3,3-dichloro-2,3-dihydro-1H-indol-2-one 
• 71-43-2 benzene 
• 92635-28-4 3,3-dibromo-1-methoxy-2-oxindole 
• 22278-19-9 ethoxy-diphenyl-acetic acid anilide 
• 91-56-5 indole-2,3-dione 
• 5554-37-0 benzilanilide 
• 108-95-2 phenol 
• 61352-09-8 2-amino-3,3-diphenyl-3H-indolenine 
• 29670-64-2 N-(2-benzoylphenyl)benzamide 
• 64-17-5 ethanol 
• 189623-31-2 1-acetyl-3,3-diphenyl-indolin-2-one 
• 119-61-9 benzophenone 
• 525-06-4 diphenyl ketene 
• 201024-81-9 C,N-diphenylnitrone 

Downstream Products

• 40863-31-8 3,3-Diphenylindoline 
• 71526-47-1 4,4-diphenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-one 
• 117007-72-4 3,3-diphenylindoline-2-thione 
• 189623-31-2 1-acetyl-3,3-diphenyl-indolin-2-one 
• 1922-81-2 1-benzyl-3,3-diphenylindolin-2-one 

Relevant academic research and scientific papers

Synthesis of functionalized 2-oxindoles by Friedel-Crafts reactions

A series of acetonyl-substituted 3-hydroxy-2-oxindoles have been prepared and reacted with arenes in superacid promoted Friedel-Crafts reactions. The product aryl-substituted 2-oxindoles are formed in generally good yields. With substituted arenes such as

Fs-ps Exciton dynamics in a stretched tetraphenylsquaraine polymer

A tetraphenylsquaraine was synthesized whose structure was elucidated by single crystal X-ray structure analysis. Unlike all known indolenine squaraines, the tetraphenylsquaraine shows an unusual nonplanar structure with the four phenyl groups pointing aw

Phosphoric Acid Catalyzed 1,2-Rearrangements of 3-Hydroxyindolenines to Indoxyls and 2-Oxindoles: Reagent-Controlled Regioselectivity Enabled by Dual Activation

A common synthetic route to indoxyl and 2-oxindole alkaloids utilizes the oxidation of indoles to 3-hydroxyindolenines, followed by acid-mediated 1,2-rearrangement. However, controlling the regioselectivity is often challenging and there is an ongoing need for new reaction conditions allowing to steer product selectivity. We report herein that phosphoric acids are ideal organocatalysts for the highly regioselective 1,2-rearrangement of 3-hydroxyindolenines to 2-oxindoles, with predictable product selectivity arising from an efficient dual activation mode.

Transition metal and base-free synthesis of 3,3-diaryl-2-oxindoles from 2,2,N-triarylacetamides

A transition metal and base-free synthesis of 3,3-diaryl-2-oxindoles has been developed from 2,2,N-triarylacetamides in the presence of montmorillonite K-10 in 1,2-dichlorobenzene under O2 balloon atmosphere.

Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides

Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.

Reactions of ortho-lithiophenyl (-hetaryl) isocyanides with carbonyl compounds: Rearrangements of 2-metalated 4H-3,1-benzoxazines

(Chemical Equation Presented) ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofura

Superacid-promoted reactions of α-ketoamides and related systems

(Chemical Equation Presented) The superacid-promoted reactions of α-hydroxy and α-ketoamides have been studied. Ionization of these compounds leads to varied aryl-substituted oxyindole products. In some cases, electrocyclization can lead to substituted fl

3-3-DI-SUBSTITUTED-OXINDOLES AS INHIBITORS OF TRANSLATION INITIATION

Compositions and methods for inhibiting translation using 3-(5-tert-Butyl-2-Hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one and/or its derivatives are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using 3-(5-tert-butyl-2-hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one and/or its derivatives are described.

Preparation of 3,3-Diaryloxindoles by superacid-induced condensations of isatins and aromatics with a combinatorial approach

3,3-Diaryloxidoles are prepared in high yields (62-99%) by reaction of isatin or substituted isatins with aromatics in triflic acid. The reaction shows a significant dependence on acid strength which suggests the formation of diprotonated, superelectrophi

29. Synthesis of Indole Derivatives by [2 + 2] Photocycloaddition of Indoline-2-thiones with Alkenes and Photodesulfurization of Indoline-2-thiones

The photochemical synthesis of indole derivatives starting from the indoline-2-thiones 1 is described. Irradiation of indoline-2-thiones 1 in the presence of alkenes 3 gave 2-alkyl-3H-indoles 4-7 or 2-alkylindoles 8-22 through the ring cleavage of the intermediates, spirocyclic amino-thietanes, initially derived by [2 + 2] cycloaddition of the C=S bond of 1 and the C=C bond of 3. Irradiation of 1 in the presence of trialkylamines 26 gave desulfurization products 27-32 and unexpected 3-alkylindoles 33-40. N-Acylindoline-2-thiones 1l-p yielded the deacylated products, indoline-2-thiones 1a-b, and ethyl esters 43 through γ-H abstraction by the excited thioamide S-atom when irradiated in CDCl3/EtOH or benzene/EtOH. Oxygen analogues 2a-d also underwent intramolecular H abstraction to give the indolin-2-ones 2e-f and ethyl esters 43 in a similar way.