79498-52-5Relevant academic research and scientific papers
Weakly Coordinating, Ketone-Directed (η5-Pentamethylcyclopentadienyl)cobalt(III)- and (η5-Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C?H Amidation of Arenes: A Route to Acridone Alkaloids
Bera, Sourav Sekhar,Sk, Md Raja,Maji, Modhu Sudan
supporting information, p. 1806 - 1811 (2019/01/14)
The weakly coordinating, ketone-directed, regioselective monoamidation of aromatic ketones, chalcone, carbazole, and benzophenones was achieved by employing high-valent cobalt and rhodium catalysis to access numerous biologically important molecular building blocks. This amidation proceeded smoothly with a variety of ketones and several amidating partners. The application of the products in the synthesis of various heterocycles, including acridones, indoles, quinoline, quinolones, quinolinones, and quinazolines, was also explored. The total synthesis of acridone-based alkaloids, namely, toddaliopsin A, toddaliopsin D, and arborinine, and the formal synthesis of acronycine and noracronycin were also accomplished by applying this method. A mechanistic study revealed this amidation reaction follows a base-assisted intermolecular electrophilic substitution pathway.
Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)-C(sp2) Bond: Synthesis of Substituted Benzoxazinones
Verma, Ajay,Kumar, Sangit
supporting information, p. 4388 - 4391 (2016/10/11)
A transition metal (TM)-free practical synthesis of biologically relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C(sp3)-C(sp2) bond employing iodine, sodium bicarbonate, and tbutyl hydroperoxide in DMSO at 95 °C. Control experiments and Density Functional Theory (DFT) calculations suggest that the reaction involves a [1,5]H shift and extrusion of CO gas as the key steps. The extrusion of CO has also been established using PMA-PdCl2.
THE REARRANGEMENT OF HYDROPEROXYINDOLENINES
McCapra, F.,Long, P. V.
, p. 3009 - 3012 (2007/10/02)
Examination of a series of substituted 3-(hydroxyperoxy)indolenines favours a mechanism for base catalysed decomposition of the dioxetan rather than Criegee type.
