97691-25-3Relevant academic research and scientific papers
SILVER-MEDIATED OXIDATIVE DECARBOXYLATION OF CARBOXYLIC ACIDS BY PEROXOCOMPOUNDS. NEW SOURCES OF CARBON-CENTERED RADICALS FOR HETEROAROMATIC SUBSTITUTION
Minisci, Francesco,Vismara, Elena,Romano, Ugo
, p. 4803 - 4806 (1985)
The silver catalyzed oxidative decarboxylation of carboxylic acids by aroylperoxides, percarbonates and perborate provides new sources of alkyl radicals useful for selective substitution of lepidine.
Novel and convenient synthesis of substituted quinolines by copper- or palladium-catalyzed cyclodehydration of 1-(2-aminoaryl)-2-yn-1-ols
Gabriele, Bartolo,Mancuso, Raffaella,Salerno, Giuseppe,Ruffolo, Giuseppe,Plastina, Pierluigi
, p. 6873 - 6877 (2008/02/10)
(Chemical Equation Presented) A general and convenient synthesis of substituted quinolines by regioselective copper- or palladium-catalyzed 6-endo-dig cyclization-dehydration of 1-(2-aminoaryl)-2-yn-1-ols is reported. The crude substrates were easily obtained by the Grignard reaction between the appropriate alkynylmagnesium bromide and 2-aminoaryl ketones and could be used without further purification for the subsequent cyclization step. Heteroannulation reactions were carried out in MeOH or DME as the solvent at 60 or 100°C in the presence of CuCl2 or PdX2 (in conjunction with 10 equiv of KX, X = Cl, I) as the catalyst to afford the quinoline derivatives in good to excellent isolated yields based on starting 1-(2-aminoaryl)-2-yn-1-ols (66-90%).
Molecule-Induced Homolysis versus "Concerted Oxenoid Oxygen Insertion" in the Oxidation of Organic Compounds by Dimethyldioxirane
Bravo, Anna,Fontana, Francesca,Fronza, Giovanni,Minisci, Francesco,Zhao, Lihua
, p. 254 - 263 (2007/10/03)
Evidence for a molecule-induced homolysis of dimethyldioxirane by several classes of organic compounds (alkanes, alkenes, ethers, alcohols, aldehydes, iododerivatives) is reported. Carbon-centered radicals, arising from alkanes, ethers, and aldehydes, are trapped by CBrCl3 or protonated quinolines. The dramatic influence of oxygen in these reactions, as well as the formation of products of induced homolysis of the dioxirane by carbon-centered radicals (CH4, CH3OH, CH3COOCH3, ROCOCH3, CH3COOCH2COCH3), strongly supports a radical mechanism. With alkenes and iodo derivatives the induced homolysis would lead to diradical intermediates, whose very fast fragmentation would prevent detection, but circumstantial evidence supports a radical mechanism.
Trapping of free-radicals in the oxidation of ethers, aldehydes and alkanes by dimethyldioxirane
Minisci, Francesco,Zhao, Lihua,Fontana, Francesca,Bravo, Anna
, p. 1895 - 1898 (2007/10/02)
Alkyl, α-oxyalkyl and acyl radical intermediates in the oxidation of alkanes, ethers and aldehydes by dimethyldioxirane are trapped by protonated quinolines and a free-radical chain is suggested for the α-acetoxylation of ketones.
A Convenient Synthesis of Substituted Quinolines by Thermal Electrocyclic Rearrangement of o-Vinyl Anils under Nonacidic Conditions
Qiang, Lin Guo,Baine, Neil H.
, p. 4218 - 4222 (2007/10/02)
Anils 8a-g (Table II) underwent smooth rearrangement and oxidation to the quinolines 9a-g at 155-200 deg C via formation of the 2-3 carbon-carbon bond.These cyclizations proceeded in high yields under nonacidic conditions.It was often possible to prepare
