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The iron-catalyzed hydrogen transfer strategy has been applied to the redox condensation of -hydroxynitrobenzene with alcohol, leading to the formation of benzoxazole derivatives. A wide range of 2-substituted benzoxazoles were synthesized in good to excellent yields without the addition of an external redox agent. A series of control experiments provided a plausible mechanism. Furthermore, the reaction system was successfully extended to the synthesis of benzothiazoles and benzimidazoles.
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http://dx.doi.org/10.1021/acs.joc.0c02191 | DOI Listing |
Future Med Chem
August 2025
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir, Turkey.
In these review series, recent reports on the design and development of analgesic molecules were reviewed. The primary aim is to examine heterocyclic frameworks involved in pain modulation and, where applicable, to establish structure - activity relationships (SARs). Currently, nine major pathways have been described for pain relief, including prostaglandin synthesis inhibition, opioid receptor modulation, sodium channel blockade, enhancement of serotonin and norepinephrine levels, cannabinoid receptor (CBR) binding, -methyl--aspartate (NMDA) receptor antagonism, transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonism, and P2X purinergic receptor blockade.
View Article and Find Full Text PDFOrg Lett
August 2025
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
A (XantPhos)Pd-catalyzed decarbonylative C-H functionalization of azoles with difluoromethyl anhydrides is reported. Under the optimized conditions, azole substrates react selectively at the C(2)-position to afford CFH-substituted benzoxazole, oxazole, benzothiazole, thiazole, and benzimidazole products. Organometallic mechanistic studies reveal that XantPhos enforces an unusual seesaw geometry of the key Pd(CFH)(carboxylate) intermediate, which may be responsible for the effectiveness of this ligand.
View Article and Find Full Text PDFDalton Trans
July 2025
School of Chemistry and Chemical Engineering, Jiangxi Provincial Key Laboratory of Functional Crystalline Materials Chemistry, Jiangxi University of Science and Technology, Ganzhou 341000, Jiangxi Province, P.R. China.
Two distinct Cd metal-organic frameworks (MOFs) with the formulas {[Cd(BBZB)(oba)]·HO} (JXUST-45) and {[Cd(BBZB)(bpdc)]·2HO} (JXUST-46) featuring 2D layer and 3D pillar-layer structures, respectively, have been prepared, which were regulated by aromatic dicarboxylate ligands (4,4'-diphenyl ether dicarboxylic acid, Hoba; 4,4'-biphenyldicarboxylic acid, Hbpdc; and 4,7-bis(1-benzimidazol-1-yl)-2,1,3-benzothiazole, BBZB). JXUST-45 and JXUST-46 can be considered good fluorescence sensors toward Al, Fe, AcO, CrO, and L-serine. Meanwhile, JXUST-45 and JXUST-46 have good thermal stability and recovery ability.
View Article and Find Full Text PDFDrug Dev Res
June 2025
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, İstanbul Okan University, İstanbul, Türkiye.
Metronidazole (MTZ) is one of the oldest and still used anti-infective nitroimidazole group drug. Although it is effective against anaerobic bacteria, protozoa, and parasites in clinical settings, it lacks efficacy against aerobic microorganisms. Due to its efficient molecular structure and synthetic usability due to the alcohol group in its framework, medicinal chemists aimed to reach new more effective molecules such as MTZ-hybrids.
View Article and Find Full Text PDFJ Org Chem
June 2025
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
The development of green and efficient methods for the construction of -heterocyclic frameworks has attracted considerable attention in organic synthesis. In this work, an electrochemical oxidative cyclization of primary amines for the synthesis of benzimidazole, benzothiazole, quinazolinone, and quinoxaline has been developed. This catalyst- and oxidant-free strategy demonstrates good functional group tolerance, up to 87% yield of N-based heterocycles in an electrochemical undivided cell under open-air conditions and is easy to scale up.
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