19490-94-9Relevant academic research and scientific papers
Reductive arylation of aliphatic and aromatic aldehydes with cyanoarenes by electrolysis for the synthesis of alcohols
Zhang, Xiao,Yang, Chao,Gao, Han,Wang, Lei,Guo, Lin,Xia, Wujiong
supporting information, p. 3472 - 3476 (2021/05/10)
An electroreductive arylation reaction of aliphatic and aromatic aldehydes as well as ketones with electro-deficient (hetero)arenes is described. A variety of cyano(hetero)arenes and carbonyl compounds, especially aliphatic aldehydes, have been examined, providing secondary and tertiary alcohols in moderate to good yields. Mechanistic studies, including cyclic voltammetry (CV), electron paramagnetic resonance (EPR), and divided-cell experiments, support the generation of aliphatic ketyl radicals and persistent heteroaryl radical anions via cathodic reduction followed by radical-radical cross-coupling.
Iron-catalysed 1,2-aryl migration of tertiary azides
Wei, Kaijie,Yang, Tonghao,Chen, Qing,Liang, Siyu,Yu, Wei
supporting information, p. 11685 - 11688 (2020/10/19)
1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.
Metal-Free Synthesis of C-4 Substituted Pyridine Derivatives Using Pyridine-boryl Radicals via a Radical Addition/Coupling Mechanism: A Combined Computational and Experimental Study
Wang, Guoqiang,Cao, Jia,Gao, Liuzhou,Chen, Wenxin,Huang, Wenhao,Cheng, Xu,Li, Shuhua
supporting information, p. 3904 - 3910 (2017/03/20)
Density functional theory investigations revealed that the pyridine-boryl radical generated in situ using 4-cyanopyridine and bis(pinacolato)diboron could be used as a bifunctional “reagent”, which serves as not only a pyridine precursor but also a boryl radical. With the unique reactivity of such radicals, 4-substituted pyridine derivatives could be synthesized using α,β-unsaturated ketones and 4-cyanopyridine via a novel radical addition/C-C coupling mechanism. Several controlled experiments were conducted to provide supportive evidence for the proposed mechanism. In addition to enones, the scope could be extended to a wide range of boryl radical acceptors, including various aldehydes and ketones, aryl imines and alkynones. Lastly, this transformation was applied in the late-stage modification of a complicated pharmaceutical molecule.
A succinic acid many west pulls sensitively impurity A preparation method (by machine translation)
-
Paragraph 0045; 0046; 0057; 0058; 0069; 0070; 0081; 0082;, (2017/11/04)
The invention discloses a succinic acid many west pulls sensitively impurity A preparation method, relates to the technical field of chemical industry, comprising the following steps: to 4 - acetyl pyridine as raw material, addition reaction with the Grig
Iron-Catalyzed Aerobic Oxidation of (Alkyl)(aryl)azinylmethanes
Sterckx, Hans,Sambiagio, Carlo,Lemière, Filip,Tehrani, Kourosch Abbaspour,Maes, Bert U. W.
, p. 1564 - 1570 (2017/08/11)
An iron-catalyzed aerobic oxidation of (alkyl)(aryl)azinylmethanes has been developed leading to tertiary alcohols in moderate to good yields. Hock rearrangement was identified as a major side reaction leading to a complex mixture of undesired products. Addition of thiourea sometimes allows inhibiting this side reaction and steers the reaction towards the desired products.
Naphthalene-catalysed lithiation of chlorinated nitrogenated aromatic heterocycles and reaction with electrophiles
Gómez, Inmaculada,Alonso, Emma,Ramón, Diego J.,Yus, Miguel
, p. 4043 - 4052 (2007/10/03)
Naphthalene catalysed reductive lithiation of various chloroazines (1, 7, 10, 13) in the presence of different electrophiles yields, after hydrolysis, the expected functionalised heterocycles with one (2, 8), two (11, 14a-d) and three nitrogen atoms in the ring (14e,f). This methodology allowed us to trap in situ the lithium imine derived from the reaction of 2- pyridyllithium with benzonitrile, by reaction with a Grignard reagent in the presence of titanium alkoxides. 2,4-Dimethoxypyrimidines (14a,c,d) are demethylated under acidic conditions to give the corresponding uracil derivatives 16. (C) 2000 Elsevier Science Ltd.
Kinetics of the self-assembly of α-cyclodextrin [2]pseudorotaxanes with 1,12-bis(4-(α-alkyl-α-methylmethanol)pyridinium)dodecane dications in aqueous solution
Smith, A. Catherine,Macartney, Donal H.
, p. 9243 - 9251 (2007/10/03)
The kinetics and thermodynamics of the self-assembly of a series of [2]pseudorotaxanes comprised of α-cyclodextrin (α-CD) and racemic 1,12- bis(4-(α-alkyl-α-methylmethanol)pyridinium)dodecane dications (L(CH2)12L2+) in aqueous solutions have been investigated using 1H NMR spectroscopy. The mechanism of assembly involves inclusion of the α-methyl- α-alkylmethanol substituent groups (-C(CH3)(OH)R, where R = Me, Et, Pr, Bu, allyl, and 4-butenyl) by α-CD, followed by a rate-determining passage of the cyclodextrin over the pyridinium group onto the dodecamethylene chain. Dicationic threads containing end groups with R = Ph or i-Pr or where L = 4- (α,α-diethylmethanol)-pyridinium did not form α-cyclodextrin pseudorotaxanes, even after prolonged heating. The trends in the rate and activation parameters may be related to the size, shape, and hydrophobicity of the alkyl substituents and are compared with several other systems from the literature. An increase in the length and hydrophobicity of the alkyl group increases the strength of end group inclusion and decreases the rate of threading. In addition, the presence of unsaturation in the alkyl substituent (allyl vs propyl and 4-butenyl vs butyl) results in an increase in the threading rate constant.
A novel hydroxyalkyl-decyanation of 4-pyridinecarbonitrile: A facile selective synthesis of 4-pyridinemethanols
Zeng,Cai,Gu
, p. 7275 - 7276 (2007/10/02)
Reactions of 4-pyridinecarbonitrile with alkali metal and ketones or aldehydes provide a convenient and useful method for synthesis of 4-pyridinemethanols in good yields.
Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogues: Synthesis and monoamine oxidase catalyzed bioactivation
Efange,Michelson,Remmel,Boudreau,Dutta,Freshler
, p. 3133 - 3138 (2007/10/02)
Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.
REACTIONS OF PYRIDYL AND QUINOLYL SULFOXIDES WITH GRIGNARD REAGENT : A CONVENIENT PREPARATION OF PYRIDYL AND QUINOLYL GRIGNARD REAGENTS
Furukawa, Naomichi,Shibutani, Tadao,Matsumura, Kazunori,Fujihara, Hisashi,Oae, Shigeru
, p. 3899 - 3902 (2007/10/02)
3-,4-Pyridyl and 4-quinolyl Grignard reagents were generated by the reaction of the corresponding phenyl sulfoxides with PhMgBr and give the adducts upon treatment with various aldehydes and ketones.The stereochemistry for the reaction was investigated.
