111888-47-2Relevant academic research and scientific papers
Divergent Syntheses of Pyridoacridine Alkaloids via Palladium-Catalyzed Reductive Cyclization with Nitro-Biarenes
Bian, Changhao,Liao, Hongze,Lin, Hou-Wen,Liu, Bo,Wang, Shuping
supporting information, p. 1905 - 1910 (2021/06/07)
A divergent and novel protocol for the preparation of both pyrido[2,3,4-kl]acridine and pyrido[4,3,2-kl]acridine alkaloids was developed. This method featured the remote palladium-catalyzed reductive cyclization with Mo(CO)6 as reductant. A wide range of substrates including three types of nitro arenes were tolerated and afforded corresponding products in good to excellent yields. This method has been successfully applied to the total synthesis of norsegoline, styelsamine C and the skeleton of necatorone.
Visible-light-driven Cadogan reaction
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 2582 - 2586 (2021/03/09)
Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
Aerobic oxidation of PdII to PdIV by active radical reactants: Direct C-H nitration and acylation of arenes via oxygenation process with molecular oxygen
Liang, Yu-Feng,Li, Xinyao,Wang, Xiaoyang,Yan, Yuepeng,Feng, Peng,Jiao, Ning
, p. 1956 - 1963 (2015/03/14)
A Pd-catalyzed aerobic oxidative C-H nitration and acylation of arenes with simple and readily available tert-butyl nitrite (TBN) and toluene as the radical precursors has been developed. Molecular oxygen is employed as the terminal oxidant and oxygen source to initiate the active radical reactants. Many different directing groups such as pyridine, pyrimidine, pyrazole, pyridol, pyridylketone, oxime, and azo groups can be employed in these novel transformations. The PdII/PdIV catalytic cycle through a radical process is the most likely pathway for these oxidative C-H nitration and acylation reactions.
Synthesis of Indazoloisoquinoline
Stanforth, S. P.
, p. 531 - 532 (2007/10/02)
Treatment of 1-(2'-nitrophenyl)isoquinoline with hot triethylphosphite afforded indazoloisoquinoline.
