1448631-97-7Relevant academic research and scientific papers
Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides
Villo, Piret,Kervefors, Gabriella,Olofsson, Berit
supporting information, p. 8810 - 8813 (2018/08/17)
Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.
Scalable Multigram Syntheses of Antimalarial 4(1H)-Quinolones ELQ-300 and P4Q-391
Namelikonda, Niranjan K.,Monastyrskyi, Andrii,Manetsch, Roman
, p. 3328 - 3334 (2017/06/29)
Antimalarial compounds ELQ-300 and P4Q-391 are highly potent against the blood and the liver stages of the Plasmodium parasite and also possess potent transmission-blocking activity. Gram amounts of these two compounds were required for extensive assessment of in vivo efficacy, pharmacokinetics, and safety. Several deficiencies existed in the original synthetic routes of ELQ-300 and P4Q-391 including reliance on toxic heavy-metal reagents, harsh reaction conditions, and several low-yielding steps. Herein, we report the development of two alternative syntheses, which are reliable, high yielding, scalable, and have the potential to become a route of choice at process scale.
Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines
Beaud, Rodolphe,Phipps, Robert J.,Gaunt, Matthew J.
supporting information, p. 13183 - 13186 (2016/10/22)
Catalytic synthesis of nonracemic P-chiral phosphine derivatives remains a significant challenge. Here we report Cu-catalyzed enantioselective arylation of secondary phosphine oxides with diaryliodonium salts for the synthesis of tertiary phosphine oxides
Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: An immediate access to diverse 3-aryl-4(1 H)-quinolones
Monastyrskyi, Andrii,Namelikonda, Niranjan K.,Manetsch, Roman
, p. 2513 - 2520 (2015/03/18)
A clean arylation protocol of ethyl acetoacetate was developed using hypervalent diaryliodonium salts under mild and metal-free conditions. The scope of the reaction, using symmetric and unsymmetric iodonium salts with varying sterics and electronics, was examined. Further, this method has been applied for the synthesis of antimalarial compound ELQ-300, which is currently in preclinical development.
