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
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.
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.
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
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.
α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines
Baker, Kristen M.,Tallon, Amanda,Loach, Richard P.,Bercher, Olivia P.,Perry, Matthew A.,Watson, Mary P.
supporting information, p. 7735 - 7739 (2021/10/20)
A deaminative reaction of Katritzky alkylpyridinium salts and sulfinimines has been developed to deliver enantiopure α-chiral amines. The success of this method relied on the discovery of a thermally promoted deamination via single-electron transfer of an anion-πcomplex of the alkylpyridinium cation with potassium carbonate. This method boasts excellent diastereoselectivity over the α-stereocenter as well as broad functional group and heterocycle tolerance.
Synthesis of Kr?hnke pyridines through iron-catalyzed oxidative condensation/double alkynylation/amination cascade strategy
Gopalaiah, Kovuru,Choudhary, Renu
supporting information, (2021/09/15)
An efficient protocol for the synthesis of symmetrical and unsymmetrical 2,4,6-trisubstituted pyridines via oxidative cascade annulation of arylacetylenes with benzylamines has been developed. The reaction proceeds smoothly utilizing iron(II) triflate as a catalyst and molecular oxygen as an oxidant with broad substrate scope. Mechanistic studies reveal that the reaction may be experiences an oxidative condensation followed by double alkynylation and amination process.
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.
