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
Synthesis of Poly-Substituted Pyridines via Noble-Metal-Free Cycloaddition of Ketones and Imines
Mao, Yeting,Mao, Hong,Xu, Jiaojiao,Liu, Tianqi,Liu, Bingxin,Tan, Qitao,Ding, Chang-Hua,Xu, Bin
supporting information, p. 3905 - 3908 (2021/10/20)
An eco-friendly and noble-metal-free formal [4+2] cycloaddition reaction was developed for the efficient synthesis of biologically interesting poly-substituted pyridines from easily available ketones and imines, whereby two sequential C?C bonds are formed. The given approach features a unique synthetic strategy of imines and ketones with wide substrate scope, good functional group tolerance, mild conditions and operational simplicity, which represents a more direct pathway to synthesize poly-substituted pyridines than traditional methods.
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.
