580-35-8Relevant academic research and scientific papers
Carbon-Nitrogen Bond Cleavage in ?-Radicals derived by Reduction of N-Benzyl- and N-Allyl-pyridinium Salts
Grimshaw, James,Moore, Shirley,Thompson, Norris,Trocha-Grimshaw, Jadwiga
, p. 783 - 784 (1983)
Certain 1-alkyl-2,4,6-trisubstituted pyridinium salts form ?-radicals by electrochemical reduction which are stable in dimethylformamide on the time scale of cyclic voltammetry, whereas the corresponding 1-benzyl and 1-allyl compounds undergo carbon-nitrogen bond cleavage at measured rates which are dependent on the size of the 2,6-substituents.
I2-Promoted Condensation/Cyclization of Aryl Methyl Ketones with Anilines for Facile Synthesis of 1,2,4-Triarylpyrroles
Hui, Xu,Wang, Fang-Jian,Ming, Xin,Zhang, Ze
, p. 925 - 929 (2016)
A novel iodine-mediated cascade condensation-cyclization of aryl methyl ketones with anilines has been successfully developed. According to this strategy, a variety of 1,2,4-triarylpyrroles were straightforwardly synthesized in moderate to good yields from very simple and readily available starting materials. A tentative reaction mechanism is presented. A novel iodine-mediated cascade condensation/cyclization of aryl methyl ketones with anilines has been successfully developed. According to this straightforward strategy, a variety of 1,2,4-triarylpyrroles were synthesized in moderate to good yields from very simple and readily available starting materials.
Three-component reaction access to: S-alkyl dithiocarbamates under visible-light irradiation conditions in water
Cui, Wenwen,Deng, Qirong,Li, Xuehao,Lv, Jian,Song, Xiuyan,Yang, Daoshan
, p. 1302 - 1307 (2022/02/17)
An efficient and environmentally friendly visible-light promoted method for the synthesis of S-alkyl dithiocarbamates with a broad substrate scope and good functional group tolerance in water has been developed. Most appealingly, the reaction can proceed smoothly without any external photocatalyst being added. This method opens a new avenue towards S-alkyl dithiocarbamates, thus promising their broad applications in pharmaceutical chemistry and sulfur chemistry. This journal is
Iron-Catalyzed Synthesis of Pyridines from α,β-Unsaturated Ketoxime Acetates and N -Acetyl Enamides
Xu, Gaochen,Yan, Huan,Zhang, Sai,Wu, Qinghuan,Duan, Jindian,Guo, Kai
supporting information, p. 283 - 287 (2021/12/03)
A new method of FeCl2-catalyzed [4+2] annulation of α,β-unsaturated ketoxime acetates with N-acetyl enamides in batch and flow is reported. The current strategy features low-cost catalytic system, use of electron-rich olefins, operational simplicity, and broad substrate scope, thus providing a facile and efficient access to substituted pyridines in moderate to good yields.
TMSOTf-mediated Kr?hnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
Chan, Chieh-Kai,Chung, Yi-Hsiu,Wang, Cheng-Chung
, p. 8263 - 8273 (2022/04/07)
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.
Convenient one-pot synthesis of 1,2,4-oxadiazoles and 2,4,6-triarylpyridines using graphene oxide (GO) as a metal-free catalyst: Importance of dual catalytic activity
Basak, Puja,Dey, Sourav,Ghosh, Pranab
, p. 32106 - 32118 (2021/12/02)
A convenient and efficient process for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 2,4,6-triarylpyridines has been described using an inexpensive, environmentally benign, metal-free heterogeneous carbocatalyst, graphene oxide (GO). GO plays a dual role of an oxidizing agent and solid acid catalyst for synthesizing 1,2,4-oxadiazoles and triarylpyridines. This dual catalytic activity of GO is due to the presence of oxygenated functional groups which are distributed on the nanosheets of graphene oxide. A broad scope of substrate applicability and good sustainability is offered in this developed protocol. The results of a few control experiments reveal a plausible mechanism and the role of GO as a catalyst was confirmed by FTIR, XRD, SEM, and HR-TEM analysis.
Copper-catalyzed efficient access to 2,4,6-triphenyl pyridinesviaoxidative decarboxylative coupling of aryl acetic acids with oxime acetates
Bharat Kumar, Karasala,Chinnari, Lekkala,Shyamala, Pulipaka,Siddaiah, Vidavalur,Varaprasad, Bodala
, p. 15205 - 15209 (2021/09/06)
An efficient and concise approach for the synthesis of 2,4,6-triphenyl pyridines has been developed through copper-catalysed oxidative decarboxylative coupling of C(sp3) aryl acetic acids with oxime acetates in DMF at 150 °C under an oxygen atm
Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate
Shabalin, Dmitrii A.,Dvorko, Marina Yu.,Schmidt, Elena Yu.,Trofimov, Boris A.
supporting information, p. 2703 - 2715 (2021/04/07)
A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridinesvia t-BuOK/DMSO-promotedC-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of thein situgenerated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.
Sustainable Four-Component Annulation for the Synthesis of 2,3,4,6-Tetraarylpyridines
Ding, Yuxin,Ma, Renchao,Xiao, Xu-Qiong,Wang, Lei,Wang, Zhiming,Ma, Yongmin
, p. 3897 - 3906 (2021/03/09)
A one-pot, four-component annulation of 2,3,4,6-tetraarylpyridines from aromatic aldehydes, methyl ketones, diaryl ethanones, and ammonium acetate is described. The reaction features high functional group compatibility in air under solvent-free conditions without any additive and only water as the nontoxic byproduct, providing a strategy for the facile, economical, and eco-friendly construction of multiaryl-substituted pyridines from simple and readily available reactants.
Pyridine Skeleton Synthesis Using Acetonitrile as C4N1 Units and Solvent
Bai, Chaolumen,Guo, Huifang,Liu, Xin,Liu, Dan,Sun, Zhaorigetu,Bao, Agula,Baiyin, Menghe,Muschin, Tegshi,Bao, Yong-Sheng
, p. 12664 - 12675 (2021/09/18)
The first [3 + 2 + 1] methodology for pyridine skeleton synthesis via cascade carbopalladation/cyclization of acetonitrile, arylboronic acids, and aldehydes was developed. This reaction proceeds via six step tandem reaction sequences involving the carbopalladation reaction of acetonitrile, a nucleophilic addition, a condensation, an intramolecular Michael addition, cyclization, and aromatization. Delightfully, both palladium acetate and supported palladium nanoparticles catalyzed this reaction with similar catalytic performance. The characterization results of the fresh and used supported palladium nanoparticle catalysts indicated that the reaction might be performed via a Pd(0)/Pd(II) catalytic cycle that began with Pd(0). Furthermore, the products showed good fluorescence characteristics. The green homogeneous/heterogenous catalytic methodologies pave a new way for constructing the pyridine skeleton.
