In this report, we review the current chemistry progress and in particular the synthesis approaches of tri- and tetra-substituted imidazoles.
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http://dx.doi.org/10.1007/s11030-015-9590-6 | DOI Listing |
Org Lett
December 2024
Guangxi Key Laboratory of Electrochemical and Magneto-Chemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China.
Rh(III)-catalyzed dual N-H and triple C-H activation/(4 + 2) annulation of 2-aryl-2,3-dihydro-1-perimidines and alkynes has been disclosed to construct 4,5,14,15-tetrasubstituted cationic azaperylenes with high yields (up to 95%) and broad scope. Tandem (4 + 2) annulation of 1-perimidines with vinylene carbonate and alkynes affords 4,5-disubstituted azaperylene salts, and -alkynyl 1-perimidines undergo an intra- and intermolecular annulation cascade to give 4,5,14-trisubstituted targets. Most of the intermediates were detected by ESI-MS, indicating a convincible mechanism including three possible paths.
View Article and Find Full Text PDFMolecules
August 2024
The School of Pharmacy, University College London, London WC1N 1AX, UK.
G-quadruplex (G4) sequences, which can fold into higher-order G4 structures, are abundant in the human genome and are over-represented in the promoter regions of many genes involved in human cancer initiation, progression, and metastasis. They are plausible targets for G4-binding small molecules, which would, in the case of promoter G4s, result in the transcriptional downregulation of these genes. However, structural information is currently available on only a very small number of G4s and their ligand complexes.
View Article and Find Full Text PDFDalton Trans
August 2024
Department of Chemistry, Indian Institute of Technology, Kharagpur, 721 302, Kharagpur, India.
In this study, the reaction between 2-(3,5-dimethylpyrazolylmethyl)-5-(dimethylaminomethyl)pyrrole and thiophenol under heating conditions afforded the new ligand 2-(3,5-dimethylpyrazolylmethyl)-5-(phenylthiomethyl)pyrrole 2. The reaction of 2 with -chloroperbenzoic acid provided sulfoxide 3 and sulfone 4 group-containing ligands. The reaction of 2 with copper(I) halides provided the binuclear complexes [Cu(μ-X){μ-CHN-2-(CHMepz)-5-(CHSPh)-κ-S,N}] (X = Cl, Br and I, 5-7) in high yields.
View Article and Find Full Text PDFChem Sci
July 2024
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 P. R. China
Herein, we present an attractive organocatalytic asymmetric addition of P-nucleophiles to five-membered cyclic -sulfonyl imines facilitated by phosphonium salt catalysis, enabling the highly enantioselective synthesis of tri- and tetra-substituted cyclic phosphorus-containing benzosultams. With this protocol, various cyclic α-aminophosphonates were efficiently synthesized with high yields and exceptional enantioselectivities (up to >99% ee) under mild reaction conditions. The utility and practicality of this method were demonstrated through gram-scale reactions and straightforward elaborations.
View Article and Find Full Text PDFOrg Lett
July 2024
Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.
The reduction of alkenes to their respective alkanes is one of the most important transformations in organic chemistry, given the abundance of natural and commercial olefins. Metal-catalyzed hydrogenation is the most common way to reduce alkenes; however, the use of H gas in combination with the precious metals required for these conditions can be impractical, dangerous, and expensive. More complex substrates often require extremely high pressures of H, further emphasizing the safety concerns associated with these hydrogenation reactions.
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