73120-22-6Relevant academic research and scientific papers
2,4- and 2,5-disubstituted arylthiazoles: Rapid synthesis by C-H coupling and biological evaluation
Lohrey, Lilia,Uehara, Takahiro N.,Tani, Satoshi,Yamaguchi, Junichiro,Humpf, Hans-Ulrich,Itami, Kenichiro
supporting information, p. 3387 - 3394 (2014/06/09)
Life-threatening infections caused by bacteria that have developed resistance to common antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem in hospitals and other areas all over the world. Thus, the development of an effective class of antibiotics against these bacteria is an urgent subject. Herein, we report a step-economical and diversity-oriented synthesis of a series of 2-arylidenehydrazinyl-4- arylthiazole and 2-arylidenehydrazinyl-5-arylthiazole analogues that utilizes C-H coupling methodologies. A library of 54 new congeners were synthesized and tested for their biological potential. Moreover, new knowledge regarding the structure-activity relationships (SARs) of these heterobiaryl compounds was collected. Copyright
Etherification of functionalized phenols with chloroheteroarenes at low palladium loading: Theoretical assessment of the role of triphosphane ligands in C-O reductive elimination
Platon, Melanie,Cui, Luchao,Mom, Sophal,Richard, Philippe,Saeys, Mark,Hierso, Jean-Cyrille
supporting information; experimental part, p. 3403 - 3414 (2012/02/02)
The present study highlights the potential of robust tridentate ferrocenylphosphanes with controlled conformation as catalytic auxiliaries in C-O bond formation reactions. Air-stable palladium triphosphane systems are efficient for selective heteroaryl ether synthesis by using as little as 0.2 mol% of catalyst. These findings represent an economically attractive and clean etherification of functionalized phenols, electron-rich, electron-poor and para-, meta- or ortho-substituted substrates, with heteroaryl chlorides, including pyridines, hydroxylated pyridine, pyrimidines and thiazole. The etherification tolerates very important functions in various positions, such as cyano, methoxy, amino, and fluoro groups, which is useful to synthesize bioactive molecules. DFT studies furthermore demonstrate that triphosphane ligands open up various new pathways for the C-O reductive elimination involving the third phosphane group. In particular, the rate for one of these new pathways is calculated to be about 1000 times faster than for reductive elimination from a complex with a similar ferrocenyl ligand, but without a phosphane group on the bottom Cp-ring. Coordination of the third phosphane group to the palladium(II) center is calculated to stabilize the transition state in this new pathway, thereby enhancing the reductive elimination rate. Copyright
