33357-44-7Relevant academic research and scientific papers
Radical chain monoalkylation of pyridines
Dénès, Fabrice,Jangra, Harish,Meléndez, Camilo,Mulliri, Kleni,Renaud, Philippe,Rieder, Samuel,Zipse, Hendrik
, p. 15362 - 15373 (2021/12/14)
The monoalkylation of N-methoxypyridinium salts with alkyl radicals generated from alkenes (via hydroboration with catecholborane), alkyl iodides (via iodine atom transfer) and xanthates is reported. The reaction proceeds under neutral conditions since no acid is needed to activate the heterocycle and no external oxidant is required. A rate constant for the addition of a primary radical to N-methoxylepidinium >107 M-1 s-1 was experimentally determined. This rate constant is more than one order of magnitude larger than the one measured for the addition of primary alkyl radicals to protonated lepidine demonstrating the remarkable reactivity of methoxypyridinium salts towards radicals. The reaction has been used for the preparation of unique pyridinylated terpenoids and was extended to a three-component carbopyridinylation of electron-rich alkenes including enol esters, enol ethers and enamides.
Radiation-Induced Alkylation of Quinoline Derivatives with Alcohol
Sugimori, Akira,Yamada, Tetsuo,Ishida, Hiroaki,Nose, Masayuki,Terashima, Keiko,Oohata, Noriko
, p. 3905 - 3910 (2007/10/02)
Gamma-irradiation of quinoline and its derivatives in alcohols brings about alkylation at the 2- or 4-position of pyridine ring.Hydroxyalkyl radicals play important roles in the radiation-induced alkylation with alcohol.The radiation-induced substitution of CF3CH2- and CF3CH(OH)- for H in pyridine and pyrimidine rings occurs in low yields.
