A one-pot regioselective bis-Suzuki-Miyaura or Suzuki-Miyaura/Sonogashira reaction on 2,4-dibromo-1-methyl-5-nitro-1-imidazole under microwave heating was developed. This method is applicable to a wide range of (hetero)arylboronic acids and terminal alkynes. Additionally, this approach provides a simple and efficient way to synthesize 2,4-disubstituted 5-nitroimidazole derivatives with antibacterial and antiparasitic properties.
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http://dx.doi.org/10.3390/molecules22081278 | DOI Listing |
RSC Adv
January 2025
Department of Organic Chemistry, Faculty of Chemistry, Alzahra University Vanak Tehran 1993893973 Iran
In this work, we present an efficient strategy for the straightforward synthesis of functionalized 1,6-dihydropyridine derivatives a three-component reaction of 3-vinylchromones, aromatic aldehydes, and ammonium acetate. A tandem procedure including NH aldimine formation/Michael-type addition/opening of the pyrone ring/isomerization/6π-electrocyclization/[1,5]-H shift allows rapid access to a series of dihydropyridines bearing an -hydroxybenzoyl and a benzoyl scaffold in good yields. Readily available precursors, simple heating conditions, and operational simplicity are some highlighted advantages of this transformation.
View Article and Find Full Text PDFMacromol Rapid Commun
January 2025
Chimie ParisTech, CNRS, Institut de Recherche de Chimie Paris, PSL University, Paris, 75005, France.
The development of catalysts that are both robust and highly active at room temperature can often be seen as a major challenge in anionic polymerization. However, these properties are desirable for polymer synthesis because they allow for easy and sustainable production of interesting materials. Here, iron and magnesium complexes are used to form in situ generated metalate complexes that are shown to be highly active in the room temperature copolymerization of methyl methacrylate and lactide.
View Article and Find Full Text PDFSci Rep
January 2025
Department of Chemistry, Yazd University, Yazd, Iran.
A new humic acid-based nanomagnetic copper(II) composite was prepared and used as an eco-friendly recoverable catalyst for synthesizing 1,4-disubstituted 1,2,3-triazoles. The synthesis was done via the three-component click reaction of alkyl halide, sodium azide, and terminal alkyne with good to excellent yield. A simple magnetic copper acetate composite, FeO@HA-Cu(OAc), was prepared using humic acid and characterized by SEM, TEM, XRD, EDX, EDS-mapping, VSM, TGA, AAS, and FT-IR.
View Article and Find Full Text PDFChem Asian J
January 2025
Chiang Mai University, Chemistry, 239 Huay Kaew Road, Muang District, 50200, Chiang Mai, THAILAND.
The Ph3P-I2-mediated reactions between isatins and amines were extensively investigated leading to the discovery of highly selective and divergent routes toward the synthesis of two distinct classes of indole-based frameworks. Through a strategic design of the reaction paths, we overcome potential side reactions to achieve convenient and straightforward one-pot methods to access either indoloquinazolines with C-12 carboxamide or 2-aminosubstituted indol-3-ones using the same reagent system. Mechanistic studies reveal the role of Ph3P-I2 in governing product selectivity, providing an efficient route to novel fused-indolone derivatives with promising applications in drug discovery and medicinal chemistry.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Molecular Synthesis Center, Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
2-Deoxy-β-glycosides are essential components of natural products and pharmaceuticals; however, the corresponding 2-deoxy-β-glycosidic bonds are challenging to chemically construct. Herein, we describe an efficient catalytic protocol for synthesizing 2-deoxy-β-glycosides via either IPrAuNTf-catalyzed activation of a unique 1,2--positioned C2--propargyl xanthate (OSPX) leaving group or (PhO)PAuNTf-catalyzed activation of a 1,2--C2--alkynylbenzoate (OABz) substituent of the corresponding thioglycosides. These activation processes trigger 1,2-alkyl/arylthio-migration glycosylation, enabling the synthesis of structurally diverse 2-deoxy-β-glycosides under mild reaction conditions.
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