C-H bond-selective arylation reaction of 4,5-dibromoimidazole with aryl iodides, catalyzed by the palladium-1,10-phenanthroline complex [Pd(phen)2](PF6)2, has been developed. The process tolerates the presence of a variety of functional groups on the aryl halide substrates. The products formed in these reactions were transformed to a variety of polyfunctionalized imidazoles by taking advantage of selective reactions of remaining C-Br bonds.
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RSC Adv
November 2021
Department of Chemistry, Faculty of Science, Mansoura University Mansoura 35516 Egypt.
This review emphasizes recent developments in synthetic routes of 3-(bromoacetyl)coumarin derivatives. Also, chemical reactions of 3-(bromoacetyl)coumarins as versatile building blocks in the preparation of critical polyfunctionalized heterocyclic systems and other industrially significant scaffolds are described. Recent advances of 3-(bromoacetyl)coumarins as attractive starting points towards a wide scale of five and six-membered heterocyclic systems such as thiophenes, imidazoles, pyrazoles, thiazoles, triazoles, pyrans, pyridines, thiadiazins as well as fused heterocyclic systems have been reported.
View Article and Find Full Text PDFArch Pharm (Weinheim)
March 2020
Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, Cairo, Egypt.
In the present study, a novel series of polyfunctionalized imidazopyrimidines 6a-u and 9a-d were efficiently constructed by a domino reaction between 2-imino-6-substituted-2,3-dihydropyrimidin-4(1H)-ones 4a-d or 8a-c and 2-bromoacetophenones 5a-i under mild basic conditions. The synthesized series were screened for their antibacterial activity against Staphylococcus aureus and Bacillus subtilis as Gram-positive (+) bacteria, as well as against Gram-negative (-) bacteria Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Salmonella typhi. Most of the synthesized derivatives of imidazopyrimidines 6 and 9 showed remarkable selectivity against Gram(-) bacteria over the Gram(+) ones.
View Article and Find Full Text PDFOrg Lett
September 2015
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University, Hangzhou 310058, P. R. China.
A divergent cascade annulation has been developed using readily available vinyl azides and carbazates with a wide range of substituents. Vinyl azides were successfully applied as bifunctional partners to prepare aza-pyrimidinones via 6-ring closure with carbazates as well as to construct polyfunctionalized imidazoles via 5-ring closure with N-substituted carbazates. The aza-heterocycles were obtained with high levels of chemoselectivity and excellent yields.
View Article and Find Full Text PDFJ Org Chem
August 2014
Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan.
C-H bond-selective arylation reaction of 4,5-dibromoimidazole with aryl iodides, catalyzed by the palladium-1,10-phenanthroline complex [Pd(phen)2](PF6)2, has been developed. The process tolerates the presence of a variety of functional groups on the aryl halide substrates. The products formed in these reactions were transformed to a variety of polyfunctionalized imidazoles by taking advantage of selective reactions of remaining C-Br bonds.
View Article and Find Full Text PDFAcc Chem Res
January 2009
Freie Universität Berlin, Institut für Chemie and Biochemie, Takustrasse 3, D-14195 Berlin, Germany.
As master craftsmen, modern synthetic chemists are challenged to achieve remarkable feats of efficiency and elegance toward molecular targets. The nature of this pursuit necessitates the collection of synthetic repertoires that are tried and true. With methodologies and pathways increasingly scrutinized, the adept chemist must seek out propitious tools to incorporate into the arsenal.
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