A new strategy for the metal-free decarboxylative alkoxylation of 2-picolinic acid and its derivatives is described. The three-component reaction of 2-picolinic acid or its derivatives, cyclic ethers, and BuOCl proceeded smoothly in the presence of a catalytic amount of p-chloranil to produce 2-alkoxylated pyridines with an ω-chlorine atom in satisfactory to excellent yields. New C-O and C-Cl bonds were generated in one step. The ω-C-Cl bond can be easily transformed to a C-C or C-heteroatom bond, increasing the use of 2-alkoxylated pyridine products in organic synthesis. The electronic property of the substituent linked on the pyridine ring did not influence the reactivity of the 2-picolinic acid substrates.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.8b02896 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Surface-bound Fe(0) and Fe(II) mediated by 2-picolinic acid functionalized zero-valent iron for highly Cr(VI) removal.
J Hazard Mater
November 2024
School of Engineering, China Pharmaceutical University, Nanjing 211198, China. Electronic address:
Article Synopsis
- * Characterization of PA-ZVI indicates an increased surface availability of iron (Fe(0) and Fe(II)), promoting efficient electron transfer and significantly improving chromium reduction performance, with reaction rates and adsorption capacity far exceeding those of regular ZVI.
- * Theoretical calculations reveal that PA aids in better adsorption of Cr(VI) on ZVI, resulting in a 100% conversion rate and effective performance across varying pH levels and ion conditions
Observation of oxygenated intermediates in functional mimics of aminophenol dioxygenase.
J Inorg Biochem
October 2024
Department of Chemistry, Marquette University, 1414 W. Clybourn St., Milwaukee, WI 53233, United States. Electronic address:
Aminophenol dioxygenases (APDO) are mononuclear nonheme iron enzymes that utilize dioxygen (O) to catalyze the conversion of o-aminophenols to 2-picolinic acid derivatives in metabolic pathways. This study describes the synthesis and O reactivity of two synthetic models of substrate-bound APDO: [Fe(Tp)(APH)] (1) and [Fe(Tp)(APH)] (2), where Tp = hydrotris(3,5-dimethylpyrazole-1-yl)borate, APH = 4,6-di-tert-butyl-2-aminophenolate, and APH = 4-tert-butyl-2-aminophenolate. Both Fe(II) complexes behave as functional APDO mimics, as exposure to O results in oxidative CC bond cleavage of the o-aminophenolate ligand.
View Article and Find Full Text PDFCycloplatination of symmetrical ,',''-triarylguanidines, (ArNH)C[double bond, length as m-dash]NAr with -[Pt(TFA)(S(O)Me)] in toluene afforded -[Pt(TAG)(TFA)(S(O)Me)] (TAG = triarylguanidinate(1-)-κ,κ; TFA = OC(O)CF; 6-9) in 75-82% yields. The reactions of 6-9 and the previously known -[Pt(TAG)X(S(O)Me)] (X = Cl (1) and TFA (2-5)) with acetylacetone (acacH) or 2-picolinic acid (picH) in the presence of a base afforded [Pt(TAG)(acac)] (acac = acetylacetonate-κ,'; 10-18) and [Pt(TAG)(pic)] (pic = 2-picolinate-κ,κ; 19) in high yields. The new complexes were characterised by analytical, IR and multinuclear NMR spectroscopies.
View Article and Find Full Text PDFInvestigation into the Synthesis, Bioactivity, and Mechanism of Action of the Novel 6-Pyrazolyl-2-picolinic Acid as a Herbicide.
J Agric Food Chem
April 2024
Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
A series of new 4-amino-3,5-dicholo-6-(5-aryl-substituted-1-pyrazol-1-yl)-2-picolinic acid compounds were designed and prepared to discover herbicidal molecules. The inhibitory activities of all new compounds against the root growth of were assayed. On the whole, the new synthesized compounds displayed good inhibition effects and had excellent herbicidal activities on root growth of weed at 500 μM.
View Article and Find Full Text PDFExploring the Mechanism of Immediate Analgesia Induced by Tuina Intervention on Minor Chronic Constriction Injury in Rats Using LC-MS.
J Pain Res
January 2024
School of Acupuncture-Moxibustion and Tuina, Beijing University of Chinese Medicine, Beijing, People's Republic of China.
Purpose: This study aimed to investigate changes in metabolomic expression in the spinal dorsal horn (SDH) and thalamus during a Tuina session, aiming to elucidate the mechanism of immediate analgesia.
Methods: The rats were randomly divided into three groups: the Sham group, the Model group, and the Tuina group. A minor chronic constriction injury (minor CCI) model was established in both the Model group and the Tuina group.
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!