35887-49-1

Upstream product

• 1217-89-6 1-benzylisatin 
• 100-39-0 benzyl bromide 
• 122101-01-3 N-(2-iodophenyl)-N-benzylcinnamide 
• 1589-82-8 phenylmagnesium bromide 
• 100-46-9 benzylamine 
• 36208-62-5 1,3-dibenzyl-1,3-dihydroindol-2-one 
• 102-92-1 Cinnamoyl chloride 
• 102594-26-3 1,3-dibenzyl-4-hydroxyquinolin-2(1H)-one 
• 118670-85-2 (2E)-N-(2-iodophenyl)-3-phenylprop-2-enamide 
• 615-43-0 2-iodophenylamine 
• 369651-55-8 1,3-dibenzyl-3-hydroxy-2,4(1H,3H)-quinolinedione 

Relevant academic research and scientific papers

The Power of Triplet and Singlet Oxygen in Synthesis: 2-Oxindoles, 3-Hydroxy-2-oxindoles, and Isatins from Furans

A straightforward synthesis of substituted 2-oxindoles, 3-hydroxy-2-oxindoles, and isatins has been developed. Easily accessible furans were transformed into tetrahydropyranopyrrolones by a singlet oxygen initiated cascade reaction sequence. An acid-catal

An efficient and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles via Zn-mediated barbier-type reaction under aqueous conditions

A robust and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles from isatins is described. This method introduces an ecofriendly, un-activated Zn dust, solid NH 4Cl and substrates under aqueous conditions, which has produced the product in modera

Transition-Metal-Free C-H Hydroxylation of Carbonyl Compounds

Transition metal and reductant free α-C(sp3)-H hydroxylation of carbonyl compounds are reported. This method is promoted by commercially available inexpensive KO-t-Bu and atmospheric air as an oxidant at room temperature. This unified strategy is also very facile for hydroxylation of various carbonyl compound derivatives to obtain quaternary hydroxyl compounds in excellent yield. A preliminary mechanistic investigation, supported by isotope labeling and computational studies, suggests the formation of a peroxide bond and its cleavage by in situ generated enolate.

A catalytic, mild and efficient protocol for the C-3 aerial hydroxylation of oxindoles

A mild, high yielding approach to C-3 hydroxylated oxindoles using catalytic quantities of tetrabutylammonium fluoride and air as the stoicheiometric oxidant is reported over a wide range of substitution patterns.

N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates

The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated. Georg Thieme Verlag Stuttgart.

Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: A novel sequential electrochemical radical cyclisation and hydroxylation

In recent years, intramolecular aryl radical cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride-AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon-iodine bond of N-(2-iodophenyl)-N-alkylcinnamides and their intramolecular cyclisation. The cathodic reduction of N-(2-iodophenyl)-N-alkyl-cinnamides under deaerated conditions in DMF gave 1-alkyl-3-benzylindolin-2-ones regioselectively and in the presence of oxygen yielded surprisingly 1-alkyl-3-hydroxy-3-benzylindolin-2-ones. Both these products were formed by a 5-exo-trig process in good yields. A mechanism for the formation of the products has been proposed through the use of cyclic voltammetry, coulometry and controlled-potential electrolysis as well as deuterium labelling.

Novel ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones in aqueous alkali. The first convenient route to 2-hydroxyindoxyls

Ring contraction of 3-hydroxy-2,4(1H, 3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.