92250-13-0

Upstream product

• 59-48-3 2-oxoindole 
• 108-93-0 cyclohexanol 
• 5292-21-7 Cyclohexylacetic acid 
• 613-94-5 benzoic acid hydrazide 
• 100717-32-6 3-cyclohexyl-1H-indole 
• 3478-78-2 3-cyclohexylidene-1,3-dihydro-indol-2-one 
• 108-94-1 cyclohexanone 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 131609-15-9 5-(2-chloro-1-oxoethyl)-3-cyclohexyl-1,3-dihydro-2H-indol-2-one 
• 140701-27-5 3-Bromo-3-cyclohexyl-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester 
• 185199-40-0 3-cyclohexyl-1,3-dimethyloxindole 
• 140701-21-9 3-Cyclohexyl-2-ethoxycarbonyloxy-indole-1-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O

We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).

Manganese-Catalyzed C(α)-Alkylation of Oxindoles with Secondary Alcohols via Borrowing Hydrogen

A general and efficient C(α)-alkylation of oxindoles with unactivated secondary alcohols as alkylating agents catalyzed by a newly developed NNN-Mn(II) complex is reported. Mechanistic studies illustrate that the importance of the NH moiety in the complex and M-L cooperation play very important roles during the catalytic transformation.

C-Alkylation of Various Carbonucleophiles with Secondary Alcohols under CoIII-Catalysis

Oxindoles have been successfully α-alkylated under Cp*CoIII catalysis by a vast array of secondary alcohols, including cyclic, acyclic, symmetrical, and unsymmetrical, to produce C-alkylated oxindoles. This protocol was also extended to the α-alkylation of N,N-dimethyl barbituric acid and benzyl cyanides. The kinetic profile and other preliminary mechanistic investigations suggest a first-order reaction rate in oxindoles and catalysts. A plausible catalytic cycle is proposed on the basis of the kinetic profile, of other preliminary mechanistic investigations, and of previous mechanistic studies on similar transformations, whereas density functional theory calculations provide insight into the nature of the active species.

Preparation method of 3-substituted oxidized indole and derivative

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.

A Facile Method for the Synthesis of 3-Alkyloxindole

Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.

New One-Pot Synthesis of 3-Alkyl- and 3-(ω-Hydroxyalkyl)oxindoles from Isatins

A new and efficient one-pot procedure has been developed for the synthesis of 3-alkyl- and 3-(ω-hydroxyalkyl)oxindoles from isatins by treatment with alcohols and diols in the presence of Raney nickel, under hydrogen atmosphere. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Raney nickel-induced 3-alkylation of oxindole with alcohols and diols

New reaction conditions are described, which turn Wenkert's synthesis of 3-alkyloxindoles (Raney nickel-induced alkylation of oxindole with alcohols) into a reproducible and highly efficient synthetic tool. The method is also extended to the preparation o

Phosphodiesterase inhibitors.

A compound of formula (I), or a pharmaceutically acceptable salt thereof: in which, R1 is hydrogen, C1-6 alkyl or CH2OR6; R2 is hydrogen or C1-6 alkyl; R3 is hydrogen or C1-6 alkyl; each of W and Z, which are different, represents -CR4R5- or -(CRxRy)n-, in which, R4 is hydrogen, C1-3 alkyl, C1-3 alkylthio, C1-3 alkoxy or C1-6 alkyl phenyl; R5 is C1-3 alkyl, C1-3 alkylthio, C1-3 alkoxy, phenyl, substituted phenyl, C3-6 cycloalkyl, phenylthio, C1-6 alkyl phenyl, halo-substituted benzyl, or heteroaryl; or together R4 and R5 form a 3 to 6 membered carbocyclic ring, or a heterocyclic ring containing one or two ring oxygen, nitrogen or sulphur atoms, or R4 and R5 together form an oxo or methylene group; each of Rx and Ry is hydrogen or C1-3 alkyl; n is zero or 1; R6 is phenyl substituted aminocarbonyl, C1-6 alkoxy carbonyl-C1-6 alkyl, phenyl-C1-6 alkyl, phenyl, C3-6 cycloalkylcarbonyl, C3-6 cycloalkylcarbonyl-C1-6 alkyl, C3-6 cycloalkyl C1-6 alkyl; C1-6 alkylthiocarbonyl; halo-substituted C1-6 alkoxycarbonyl; C1-6 alkoxy C1-6 alkyleneoxycarbonyl; C1-6 alkylthio C1-6 alkyleneoxycarbonyl; C1-6 alkoxythiocarbonyl; C3-6 cycloalkyloxycarbonyl; cyano substituted C1-6 alkoxycarbonyl; di-C1-6 alkylphosphonate; C1-6 alkenyloxycarbonyl; or R6 is hydrogen when R5 is phenyl, C3-6 cycloalkyl, phenylthio, C1-6 alkylphenyl or halo-substituted benzyl; R6 is benzoyl or aminobenzoyl when R4 and R5 form a C3-6 cycloalkyl ring; R7 is hydrogen, C1-6 alkyl or halogen; X is oxygen or sulphur; and A is sulphur, oxygen or -NH-, is useful for the treatment of heart disease