424834-35-5Relevant academic research and scientific papers
A Modified Procedure for the Synthesis of 1-Arylimidazoles
Liu, Jingping,Chen, Jingbo,Zhao, Jingfeng,Zhao, Yuanhong,Li, Liang,Zhang, Hongbin
, p. 2661 - 2666 (2003)
A convenient modified process for the synthesis of 1-aromatic substituted imidazoles is provided. The protocol generally affords better yields of the sterically hindered 1-arylimidazoles.
Framework-Copper-Catalyzed C?N Cross-Coupling of Arylboronic Acids with Imidazole: Convenient and Ligand-Free Synthesis of N-Arylimidazoles
Devarajan, Nainamalai,Suresh, Palaniswamy
, p. 2953 - 2960 (2016/09/28)
A convenient and environmentally benign synthesis of N-arylimidazoles has been demonstrated by a straightforward reaction catalyzed by the unsaturated coordination sites of Cu in the copper terephthalate metal–organic framework (Cu(tpa)-MOF). A series of N-arylimidazoles has been synthesized in excellent yields by the C?N cross-coupling reaction of arylboronic acids and imidazoles catalyzed by the Cu(tpa)-MOF using ethanol as a benign solvent. The present ligand-free catalytic system proceeds smoothly under mild conditions, avoids stoichiometric Cu reagents, tolerates many functional groups, has a wide substrate scope, and is feasible with other nitrogen heterocycles. The stability and heterogeneity of the catalyst is evidenced by the results of a heterogeneity test, and the catalyst can be reused several times without a loss of activity. The easy preparation of the catalyst, its stability, recovery by simple filtration, and reusability reveal Cu(tpa) MOF as a versatile catalyst for academic and industrial applications.
Ligand-free copper-catalyzed arylation of imidazole and N,N′-carbonyldiimidazole, and microwave-assisted synthesis of N-Aryl-1H-imidazoles
Yang, Xiao-Dong,Li, Liang,Zhang, Hong-Bin
experimental part, p. 1435 - 1442 (2009/02/07)
Microwave-assisted arylation of 1H-imidazoles and N,N′- carbonyldiimidazole under ligand-free copper-mediated conditions in tetraethyl orthosilicate is reported. Valuable evidence for understanding of the Cu-catalyzed mechanism of the Ullmann reaction is
Regioselective synthesis of 1,5-diaryl-1H-imidazoles by palladium-catalyzed direct arylation of 1-aryl-1H-imidazoles
Bellina, Fabio,Cauteruccio, Silvia,Mannina, Luisa,Rossi, Renzo,Viel, Stephane
, p. 3997 - 4005 (2007/10/03)
A variety of 1,5-diaryl-1H-imidazoles have been regioselectively synthesized by direct coupling of 1-aryl-1H-imidazoles with aryl iodides or bromides in DMF in the presence of CsF as the base and a catalyst precursor consisting of a mixture of Pd(OAc)sub
Potent, orally active heterocycle-based combretastatin A-4 analogues: Synthesis, structure - Activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation
Wang, Le,Woods, Keith W.,Li, Qun,Barr, Kenneth J.,McCroskey, Richard W.,Hannick, Steven M.,Gherke, Laura,Credo, R. Bruce,Hui, Yu-Hua,Marsh, Kennan,Warner, Robert,Lee, Jang Y.,Zielinski-Mozng, Nicolette,Frost, David,Rosenberg, Saul H.,Sham, Hing L.
, p. 1697 - 1711 (2007/10/03)
The synthesis and structure - activity relationship study of a series of compounds with heterocycles in place of the cis double bond in combretastatin A-4 (CA-4) are described. Substituted tosylmethyl isocyanides were found to be the key intermediates in construction of the heterocycles. Cytotoxicities of the heterocycle-based CA-4 analogues were evaluated against NCI-H460 and HCT-15 cancer cell lines. 3-Amino-4-methoxyphenyl and N-methyl-indol-5-yl were the best replacements for the 3-hydroxy-4-methoxyphenyl in CA-4. 4,5-Disubstituted imidazole was found to be the best for the replacement of the cis double bond in CA-4. Medicinal chemistry efforts led to the discovery of compounds 24h and 25f that were found to be 32 and 82% bioavailable, respectively, in rat. Evaluation of 24h and 25f against murine M5076 reticulum sarcoma in mice revealed that both compounds were orally efficacious with an increase in life span of 38.5 and 40.5%, respectively.
