855239-80-4Relevant academic research and scientific papers
Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More-Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420
Patel, Nitinchandra D.,Wei, Xudong,Byrne, Denis,Narayanan, Bikshandarkoil A.,Pennino, Scott,Sarvestani, Max,Saha, Anjan,Haddad, Nizar,Kapadia, Suresh,Lorenz, Jon C.,Decroos, Philomen,Ye, Andrew,Lee, Heewon,Grinberg, Nelu,Hossain, Azad,Busacca, Carl A.,Yee, Nathan K.,Senanayake, Chris H.
, p. 8339 - 8351 (2020)
An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.
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
, 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.
Rh(iii)-Catalyzed: Ortho -C-(sp2)-H amidation of ketones and aldehydes under synergistic ligand-accelerated catalysis
Hande, Akshay Ekanath,Ramesh, Vinay Bapu,Prabhu, Kandikere Ramaiah
supporting information, p. 12113 - 12116 (2018/11/21)
Rh(iii)-Catalyzed ortho-C-H amidation of ketones and aldehydes under cooperative metal organocatalysis has been utilized for synthesizing various ortho-amidocarbonyl analogs, and the reaction for the aldehyde proceeds at ambient temperature. The aniline derivative 3,5-bis(trifluoromethyl)aniline promotes the amidation reaction via a transient imine directing group. The efficient amidation agent is dioxazolone. The synthetic utility has been demonstrated in the synthesis of quindolinone alkaloids.
A mild, one-pot synthesis of 4-quinolones via sequential Pd-catalyzed amidation and base-promoted cyclization
Huang, Jinkun,Chen, Ying,King, Anthony O.,Dilmeghani, Mina,Larsen, Robert D.,Faul, Margaret M.
supporting information; experimental part, p. 2609 - 2612 (2009/05/27)
(Chemical Equation Presented) A mild, one-pot synthesis of 4-quinolones is described. Under the optimal conditions, a variety of 2-substituted 4-quinolones were synthesized via sequential palladium-catalyzed amidation of 2′-bromoacetophenones followed by base-promoted intramolecular cyclization.
