5191-54-8Relevant articles and documents
Acylation of 2-benzylpyridine N-oxides and subsequent in situ [3,3]-sigamatropic rearrangement reaction
Antilla, Jon C.,Jing, Hua-qing,Li, Hong-liang
supporting information, (2020/09/22)
An effective method for the acylation of 2-benzylpyridine N-oxides and their fast in situ [3,3]-sigmatropic rearrangement was reported. This transformation has a wide substrate scope under mild conditions, giving moderate to excellent yields. The application for the synthesis of chiral phenyl-2-pyridylmethanol products was briefly explored. Furthermore, an interesting example of tandem substitution and in situ [3,3]-sigamatropic rearrangement of 2-benzylpyridine N-oxide with benzenecarboximidoyl chloride was reported.
Catalytic Selective Metal-Free Cross-Coupling of Heteroaromatic N-Oxides with Organosilanes
Puthanveedu, Mahesh,Polychronidou, Vasiliki,Antonchick, Andrey P.
supporting information, p. 3407 - 3411 (2019/05/10)
A metal-free, regioselective C-H functionalization of heteroaromatic N-oxides has been developed. The method enables the synthesis of various benzylated and alkynylated N-heterocycles in a transition-metal-free manner employing organosilanes as coupling partners. The unanticipated reactivity has been exploited for the synthesis of a number of symmetrical disubstituted acetylenes from ethynyltrimethylsilane via carbon-silicon bond metathesis.
Photocatalyzed ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage
Zhou, Wang,Miura, Tomoya,Murakami, Masahiro
supporting information, p. 5139 - 5142 (2018/05/30)
A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon–carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.
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.
Palladium-Catalyzed Arylation of Benzylic C-H Bonds of Azaarylmethanes with Aryl Sulfides
Gao, Ke,Yamamoto, Keita,Nogi, Keisuke,Yorimitsu, Hideki
supporting information, p. 2956 - 2960 (2017/10/06)
Benzylic C-H arylation of azaarylmethanes with aryl sulfides has been developed by using a Pd-NHC catalyst and an amide base. Various azaarylmethanes and aryl sulfides were involved in the reaction to afford the corresponding diarylmethanes in good to excellent yields. Moreover, triarylmethane synthesis was accomplished through iterative arylations of 2- or 4-methylpyridine with two different aryl sulfides.
Palladium-catalyzed decarboxylative couplings of 2-(2-Azaaryl)acetates with aryl halides and triflates
Shang, Rui,Yang, Zhi-Wei,Wang, Yan,Zhang, Song-Lin,Liu, Lei
supporting information; experimental part, p. 14391 - 14393 (2010/12/19)
Pd-catalyzed decarboxylative cross-couplings of 2-(2-azaaryl)acetates with aryl halides and triflates have been discovered. This reaction is potentially useful for the synthesis of some functionalized pyridines, quinolines, pyrazines, benzoxazoles, and benzothiazoles. Theoretical analysis shows that the nitrogen atom at the 2-position of the heteroaromatics directly coordinates to Pd(II) in the decarboxylation transition state.
Site selective processes: A combined theoretical and experimental investigation of thermally activated tautomerization processes in 2(2,4-dinitrobenzyl) pyridine derivatives
Khatib,Tal,Godsi,Peskin,Eichen
, p. 6753 - 6761 (2007/10/03)
The thermally activated NH→CH tautomerization process in crystals of 2(2,4-dinitrobenzyl) pyridine derivatives was investigated. The results indicate the absence of any trivial molecular structure-reactivity correlation, in contrast to what is found for similar systems in solutions. The absence of molecular structure-reactivity correlation in the crystalline state is attributed to the participation of neighboring molecules in the proton transfer process. A combined experimental and theoretical approach is presented and applied to the study of the tautomerization reaction in crystalline environments. (C) 2000 Elsevier Science Ltd.
A New Route for the Synthesis of 2-Amino-biphenyls Involving Enamine Rearrangement of Pyridinium Salts
Fadda, A. A.,El-Morsy, S. S.
, p. 361 - 363 (2007/10/02)
2-Benzyl-1-methylpyridinium iodides (IIa-c) undergo ring opening and recyclization reactions when heated with aq. sodium hydroxide to give 2-methylaminobiphenyls (IIIa-c).The effect of aq. alkylamine and alkylammonium sulphite solution on this type of reaction has also been studied.
Flash Vacuum Pyrolysis of Substituted Pyridine N-Oxides and Its Application to Syntheses of Heterocyclic Compounds
Ohsawa, Akio,Kawaguchi, Takayuki,Igeta, Hiroshi
, p. 3497 - 3503 (2007/10/02)
Flash vacuum pyrolysis of 2-picoline N-oxide gave 2-picoline, pyridine, 2-ethylpyridine, 2-vinylpyridine, 2-pyridylmethanol, bis(2-pyridyl)methane, 1,2-bis(2-pyridyl)ethane, and 1,2-bis(2-pyridyl)ethylene.These reactions are explained by intermediary participation of the 2-picolyl radical.Flash vacuum pyrolysis of methyl-substituted 2-benzylpyridine N-oxides led to methyl-substituted pyridoindoles or to benzoquinoline in moderate yields.
