Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

TMSOTf-mediated Krohnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation.

ABSTRACT: An efficient protocol for the preparation of pyridine skeletons has been successfully developed involving the TMSOTf/HMDS (trifluoromethanesulfonic acid/hexamethyldisilane) system for the intermolecular cyclization of chalcones under MW (microwave) irradiation conditions. This method provides a facile approach to synthesize 2,4,6-triaryl or 3-benzyl-2,4,6-triarylpyridines in good to excellent yields. Interestingly, the 2,6-diazabicyclo[2.2.2]oct-2-ene core was obtained by changing the acid additive to Sn(OTf)₂, and the desired product was also confirmed using X-ray single-crystal diffraction analysis.

SUBMITTER: Chan CK

PROVIDER: S-EPMC8982443 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation.

Chan Chieh-Kai CK Chung Yi-Hsiu YH Wang Cheng-Chung CC

RSC advances 20220315 13

An efficient protocol for the preparation of pyridine skeletons has been successfully developed involving the TMSOTf/HMDS (trifluoromethanesulfonic acid/hexamethyldisilane) system for the intermolecular cyclization of chalcones under MW (microwave) irradiation conditions. This method provides a facile approach to synthesize 2,4,6-triaryl or 3-benzyl-2,4,6-triarylpyridines in good to excellent yields. Interestingly, the 2,6-diazabicyclo[2.2.2]oct-2-ene core was obtained by changing the acid addit ...[more]

PMID: 35424740

Similar Datasets

TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions.

Project description:In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave heating and solvent-free conditions. The chemical structures of representative trisubstituted imidazoles were confirmed using X-ray single-crystal diffraction analysis. This synthetic method has several advantages including the involvement of mild Lewis acid, being metal- and additive-free, wide substrate scope with good to excellent yields and short reaction time. Furthermore, we demonstrate the application of the methodology in the synthesis of biologically active imidazole-based drugs.

| S-EPMC9039414 | biostudies-literature

Synthesis of pyrazolopyrimidinones using a "one-pot" approach under microwave irradiation.

Project description:A simple one-pot method for the microwave-assisted synthesis of substituted pyrazolo[1,5-a]pyrimidinones, a core scaffold in many bioactive and pharmaceutically relevant compounds, has been established. A variety of substituents was tolerated at the 2 and 5 positions, including functionalized aryls, heterocycles, and alkyl groups.

| S-EPMC6009099 | biostudies-literature

HFIP-Promoted Bischler Indole Synthesis under Microwave Irradiation.

Project description:1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) was found to be effective for the Bischler indole synthesis under microwave irradiation in the absence of a metal catalyst. Under the catalysis of HFIP, a wide range of α-amino arylacetones were successfully transformed into indole derivatives with moderate to good yields.

| S-EPMC6321335 | biostudies-literature

An efficient synthesis of pyridoxal oxime derivatives under microwave irradiation.

Project description:Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%-94%) were obtained in acetone in very short reaction times (3-5 min) as well as in the solvent-free procedure (42%-78%) in very short reaction times (7-10 min) too. Effective metodologies for the preparation of pyridoxal oxime quaternary salts, having the advantagies of being eco-friendly, easy to handle, and performed in shorter reactions time are presented. The structure of compound 7, in which a 4-fluorophenacyl moiety is bonded to the pyridinium ring nitrogen atom, was unequivocally confirmed by the single-crystal X-ray diffraction method.

| S-EPMC6271574 | biostudies-literature

Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source.

Project description:In the presence of Cs2CO3, the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine derivatives accompanies the outcome of 1,3-diaryl propenes, which are also useful intermediates in organic synthesis. Thus, pyridine ring results from a formal [2+2+1+1] cyclocondensation of three alkynes with benzamides, and one of the alkynes provides one carbon, whilst benzamides provide a nitrogen source only. A new transformation of alkynes as well as new utility of benzamide are found in this work.

| S-EPMC8587654 | biostudies-literature

The Highly Efficient Synthesis of 1,2-Disubstituted Benzimidazoles Using Microwave Irradiation.

Project description:The benzimidazole ring of the heterocyclic pharmacophores is one of the most widespread and studied systems in nature. The benzimidazole derivative synthesis study is a crucial point for the development of a clinically available benzimidazole-based drug. Here, we report a simple microwave assisted method for the synthesis of 1,2-disubstituted benzimidazoles. The combination of the molar ratio of N-phenyl-o-phenylenediamine:benzaldehyde (1:1) using microwave irradiation and only 1% mol of Er(OTf)3 provides an efficient and environmental mild access to a diversity of benzimidazoles under solvent-free conditions. The proposed method allows for the obtainment of the desired products in a short time and with very high selectivity.

| S-EPMC8911685 | biostudies-literature

Green synthesis of ethyl cinnamates under microwave irradiation: photophysical properties, cytotoxicity, and cell bioimaging.

Project description:A simple and green method for the synthesis of six ethyl cinnamates was performed via Horner-Wadsworth-Emmons reaction under microwave irradiation. The photoluminescent properties of all compounds in ethyl acetate solutions were evaluated demonstrating that all compounds exhibit fluorescence. Five compounds exhibited blue emissions in the 369-442 nm range, and another compound exhibited blue-green emission at 504 nm. This last compound showed the largest Stokes shift (134 nm), and the highest quantum yield (17.8%). Two compounds showed extinction coefficient values (ε) higher than 30 000 M-1 cm-1, which are appropriate for cell bioimaging applications. In this sense, cytotoxicity assays were performed using Vero cells at different concentrations; the results showed that these compounds were not cytotoxic at the highest concentration tested (20 μg mL-1). Finally, the analysis by fluorescence microscopy for localization and cellular staining using Vero cells demonstrated that the compounds stained the cytoplasm and the nuclei in a selective way.

| S-EPMC10783162 | biostudies-literature

FeCl₃∙6H₂O/TMSBr-Catalyzed Rapid Synthesis of Dihydropyrimidinones and Dihydropyrimidinethiones under Microwave Irradiation.

Project description:An efficient and practical protocol has been developed to synthesize dihydropyrimidinones and dihydropyrimidinethiones through FeCl₃∙6H₂O/TMSBr-catalyzed three-component cyclocondensation under microwave irradiation. This approach features high yields, broad substrate scope, short reaction time, mild reaction conditions, operational simplicity and easy work-up, thus affording a versatile method for the synthesis of dihydropyrimidinones and dihydropyrimidinethiones.

| S-EPMC6151402 | biostudies-literature

Synthesis of Lead(II) Carbonate-Containing Nanoparticles Using Ultrasonication or Microwave Irradiation.

Project description:We report on the synthesis of lead(II) carbonate-containing nanoparticles using the polyol process under high-energy ultrasound or microwave irradiation as alternate energization methods. Five carbonate source precursors are used in the reaction, and the precipitation reactions generate four different crystal products, depending on the precursor. More alkaline precursors produce the hydroxy-carbonate structures (abellaite, or its potassium analog, and hydrocerussite), while the less alkaline precursors produce the simple carbonate structure (cerussite). Ultrasonication or microwave irradiation during the arrested precipitation ensures the formation of nanoparticles <100 nm in diameter in a mostly single crystalline phase in all cases, bar one. The products were characterized by powder X-ray diffraction, dynamic light scattering, electron microscopy, infrared spectroscopy, and thermal analysis. These nanoparticles are targeted as X-ray contrast agents for biological imaging, particularly of fine vasculature where small particle size is essential.

| S-EPMC11635499 | biostudies-literature

One-Pot Synthesis and Surfactant Removal from MCM-41 Using Microwave Irradiation.

Project description:This research pioneers the application of microwave irradiation as an innovative strategy for one-pot synthesis and surfactant elimination (cetyltrimethylammonium bromide-CTAB) from MCM-41, introducing a rapid and efficient methodology. MCM-41 silica is widely utilized in various applications due to its unique textural and structural properties. Nonetheless, the presence of residual surfactants after synthesis poses a challenge to its effective application. MCM-41 synthesis, conducted in a microwave reactor at 60 °C, provided a result within 0.5 to 1 h. Comprehensive analyses of structural, chemical, morphological, and surface characteristics were undertaken, with a focus on the impact of synthesis time on these properties. Surfactant extraction involved the use of ethanol as a solvent at 120 °C for 6 min within the microwave reactor. The acquired particles, coupled with the properties of textural and structural features, affirmed the efficacy of the synthesis process, resulting in the synthesis of MCM-41 within 36 min. This study presents the first instance of one-pot synthesis and surfactant removal from MCM-41 using a microwave reactor. The proposed method not only addresses the surfactant removal challenge, but also substantially accelerates the synthesis process, thereby enhancing the potential for MCM-41's application in diverse fields.

| S-EPMC10820031 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data