108-75-8Relevant articles and documents
TETRAACYLATION OF ISOBUTENE : FIRST SYNTHESIS OF 1,3,6,8-TETRAMETHYL-2,7-NAPHTHYRIDINE
Erre, Claude,Pedra, Annette,Arnaud, Michel,Roussel, Christian
, p. 515 - 518 (1984)
The tetraacetylation of isobutene has been performed in AlCl3/AcCl.Treatment of the crude reaction medium with liquid ammonia yields the title compound.
New aspect of methanesulfonyl chloride: Unusual deoxygenations of pyridine N-oxides with methanesulfonyl chloride and triethylamine
Morimoto, Yoshiki,Kurihara, Hajime,Yokoe, Chiho,Kinoshita, Takamasa
, p. 829 - 830 (1998)
Treatment of several pyridine N-oxides with an excess of methanesulfonyl chloride and triethylamine brought about a deoxygenation reaction to give efficiently the corresponding reduction products without chlorination of the pyridine nucleus.
Mechanistic Evaluation of the Transfer of Br+ from Bis(sym-collidine)bromonium Triflate to Acceptor Alkenes
Neverov, Alexei A.,Brown
, p. 5977 - 5982 (1998)
The kinetics of the reaction of bis(sym-collidine)bromonium triflate (2-Br+/OTf-) with adamantylideneadamantane (Ad=Ad), 4-penten-1-ol (4), and cyclohexene has been investigated in 1,2-dichlorethane at 25°C under a variety of conditions. The rates of all the reactions are shown to be depressed by added collidine, indicating that the first step for all is a reversible dissociation of 2-Br+/OTf- into free collidine and a reactive intermediate, coll-Br+, which is then captured by the alkene. The product of the reaction of Ad=Ad with 2-Br+/OTf- is an Ad=Ad:Br+-coll complex, while that of reaction of 4 with 2-Br+/OTf- is the cyclic ether 2-bromomethyltetrahydrofuran. The reaction with cyclohexene is more complex and involves at least two reversibly formed intermediates, suggested to be coll-Br+ and cyclohexene:Br+-coll, the latter being captured by attack of triflate to give trans-1-bromo-2-trifluoromethanesulfonylcyclohexane. Detailed kinetic analysis shows that the reactions of collidine, Ad=Ad, cyclohexene, and 4-penten-1-ol with the reactive intermediate coll-Br+ are fast but not very sensitive to the nature of the nucleophile, the second-order rate constants being 3 × 106, 1.1 × 106, 1.5 × 105, and 4.5 × 104M-1s-1, respectively. 1H NMR analysis of the reaction of trans-1-bromo-2(trifluoromethanesulfonyl)cyclohexane, produced in situ from cyclohexene and 2-Br+/OTf- in CD2Cl2, with tetrabutylammonium bromide or tetrabutylammonium acetate indicates a very rapid and quantitative production of trans-1,2-dibromocyclohexane and trans-1-bromo-2-acetoxycyclohexane, respectively.
SYNTHESIS AND PROPERTIES OF BIS(PYRIDYLMETHYLENE)MERCURY DERIVATIVES
Boev, V. I.,Dombrovskii, A. V.
, p. 649 - 651 (1981)
The action of ammonia on α- and γ-monomercurimethylenepyrylium perchlorates gave bis(pyridylmethylene)mercury derivatives, which undergo decomposition to the corresponding pyridine derivatives and mercuric chloride.
Rates of Proton Transfer between Pyridine Bases in the Gas Phase. Steric and Isotope Effects
Jasinski, Joseph M.,Brauman, John I.
, p. 2906 - 2913 (1980)
The rates of proton and deuteron transfer between various pyridine bases have been studied in the gas phase by pulsed ion cyclotron resonance spectroscopy.The results show that as the reactants become increasingly substituted in the 2 and 6 positions the reaction efficiencies decrease.Some of the least efficient reactions show a small normal kinetic deuterium isotope effect.These results are interpreted in terms of a general mechanism which includes an intrinsic barrier to proton transfer.The reaction efficiencies and isotope effects are modeled using RRKM theory, and an estimate for the intrinsic barrier height is obtained.
Microwave-assisted reduction of aromatic nitro compounds with novel oxo-rhenium complexes
Blacque, Olivier,Grieco, Gabriele
, (2021/09/16)
The reduction of several aromatic nitro compounds to amines by means of the two novel catalytic systems ([IMes]2ReOBr3)/PhSiH3 and ([Py]3ReNOBr2)/PhSiH3 under microwave irradiation is here reported. These two systems were able to perform the reduction of nitro groups with higher TON and TOF when compared with previously reported systems based on oxo-rhenium core under standard heating, although they showed a lesser broad reaction scope compared with the known systems.
NOVEL METHODS FOR PREPARATION OF SUBSTITUTED PYRIDINES AND RELATED NOVEL COMPOUNDS
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Paragraph 0195; 0218; 0219, (2020/04/10)
The present invention relates to novel methods of preparation of substituted pyridines and the compounds produced therefrom. In particular, the present invention provides efficient methods for the construction of diversely substituted pyridines, with varying substitution patterns under simple and metal-free conditions with high atom- and pot-economy and excellent functional group tolerance, and which are useful for the synthesis of natural products.
Based on supercritical fluid technology of production method of 2, 4, 6 - trimethyl pyridine (by machine translation)
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Paragraph 0025-0053, (2019/03/29)
The present invention provides a supercritical fluid technology based on 2, 4, 6 - trimethyl pyridine production method, comprising the following steps: adding the catalyst and acetone in the supercritical reaction vessel, stir, the liquid ammonia into the reactor, first pressurizing and heating make the liquid ammonia to achieve the ultra zero state, and then to continue to pressurizing and heating the acetone to achieve ultra zero state, rapid cooling, the termination of the reaction, based on supercritical fluid technology to obtain 2, 4, 6 - trimethyl pyridine elementary product; or the acetone added supercritical in the reactor, the liquid ammonia into the reactor, first pressurizing and heating make the liquid ammonia to achieve the ultra zero state, and then to continue to pressurizing and heating the acetone to achieve ultra zero state, rapid cooling, the termination of the reaction, based on supercritical fluid technology to obtain 2, 4, 6 - trimethyl pyridine and taste; finally the 2, 4, 6 - trimethyl pyridine elementary product through the rectification, based on supercritical fluid technology to obtain 2, 4, 6 - trimethyl pyridine. Preparation method of this invention is simple, efficient reaction, the yield of the product and high purity. (by machine translation)
A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate
Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Hezarkhani, Hadis Afshar
, p. 1843 - 1849 (2018/07/06)
A mild and efficient method for the oxidation of N-heteroaromatic compounds to the corresponding N-oxides using H2O2 in the presence of hexaphenyloxodiphosphnium triflate (Hendrickson reagent) in EtOH at room temperature was reported. This methodology presented relatively fast and selective reactions to afford the N-oxides in good yields. The reverse reactions, deoxygenation reactions, were also carried out under the same reaction conditions by KI to produce the tertiary amines.
Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH
Liu, Wenbo,Yang, Xiaobo,Zhou, Zhong-Zhen,Li, Chao-Jun
supporting information, p. 688 - 702 (2017/05/15)
Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.
