80560-56-1Relevant academic research and scientific papers
Pyridine compound and preparation method thereof
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Paragraph 0045-0051, (2021/02/13)
The invention provides a preparation method of a pyridine compound. The method specifically comprises the following steps: adding alpha, beta- unsaturated ketoxime acetate, ethyl pyruvate, cuprous iodide and sodium hydrosulfite into an organic solvent, uniformly performing mixing, and carrying out heating reaction to obtain the pyridine compound. The pyridine compound has the advantages of simpleoperation, mild reaction conditions, concise and rapid method, wide substrate applicability, and more complex and diverse structures and wide application prospect.
Cu-Catalyzed switchable synthesis of functionalized pyridines and pyrroles
Ling, Zheng,Xie, Fang,Gridnev, Ilya D.,Terada, Masahiro,Zhang, Wanbin
supporting information, p. 9446 - 9449 (2018/08/28)
Herein, we describe a high yielding and switchable synthesis of a range of functionalized pyridines and pyrroles via Cu-catalyzed cascade reactions with alkynes and N-sulfonyl azadienes which are readily available from saccharin. Both unsymmetrical 2,4,6-trisubstituted pyridines and multi-substituted pyrroles could be transformed into some bioactive compounds and chiral ligands.
Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines
Tan, Wei Wen,Ong, Yew Jin,Yoshikai, Naohiko
supporting information, p. 8240 - 8244 (2017/06/30)
A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.
Metal- and Solvent-Free Approach to Diversely Substituted Picolinates via Domino Reaction of Cyclic Sulfamidate Imines with β,γ-Unsaturated α-Ketocarbonyls
Biswas, Soumen,Majee, Debashis,Guin, Soumitra,Samanta, Sampak
, p. 10928 - 10938 (2017/10/27)
An efficient, solvent-free, and eco-friendly domino reaction of 5/6-membered cyclic sulfamidate imines with a variety of β, γ-unsaturated α-ketocarbonyls in neat conditions under MW irradiation promoted by DABCO as a solid organobase has been developed for the rapid construction of a novel class of densely functionalized picolinates. This interesting metal-solvent-free tactic allows a wide range of useful functionalities on the aryl rings and delivers good to excellent yields of the aforesaid aza-heterocycles within short time spans (20-40 min). A biologically promising imidazo[1,2-a]pyridine was successfully synthesized through our unique procedure.
Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita-Baylis-Hillman Acetates of Nitroolefins/Nitrodienes
Majee, Debashis,Biswas, Soumen,Mobin, Shaikh M.,Samanta, Sampak
, p. 4378 - 4385 (2016/06/09)
An interesting domino reaction of 5-membered cyclic sulfamidate imines with a variety of Morita-Baylis-Hillman acetates of nitroolefins/nitrodienes in the presence of DABCO as an organic base at 55 °C is reported for the first time. This new synthetic strategy provides a series of pharmacologically interesting 4,6-diarylpicolinates in high to excellent yields and allows several compatible functionalities on aryl rings. Moreover, the biologically interesting imidazo[1,2-a]pyridine (alpidem derivative) has been prepared in high chemical yield through a unique procedure.
Nucleophilic Displacement of N-Aryl and Heteroaryl Groups. Part 5. Conversion of 2-Aminopyridines into 2-Pyridones
Katritzky, Alan R.,Awartani, Radi
, p. 2623 - 2627 (2007/10/02)
2-Ethoxycarbonyl-1-(2-pyridyl)pyridinium cations (3) (easily prepared from 2-aminopyridine and the appropriate pyrylium salt) are converted by dilute NaOH at 25 deg C into 1-(substituted 2-pyridylcarbonyl)-2-pyridones (7).Compounds (7) are readily hydrolysed to 2-pyridones.
Kinetics and Mechanism of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 8. Conductimetric and Spectrophotometric Rate Constants for the Reactions of Pyridimium and Related Cations with Piperidine in Chlorobenzene
Katritzky, Alan R.,Ou, Yu Xiang,Ellison, Joan,Musumarra, Giuseppe
, p. 1421 - 1426 (2007/10/02)
A conductimetric method is developed to obtain rates for the title reactions for which the spectrophotometric method fails.It gives equivalent results.NN'-Dimethylthiourea displaces heterocyclic leaving groups at rates similar to those for piperidine.Compared with α-hydrogen, α-methyl groups render pyridine a less effective leaving group, whereas α-ethoxycarbonyl groups show a large rate enhancement.
Nucleophilic Displacements of N-Aryl and Heteroaryl Groups. Part 4. Pyrylium-mediated Transformations of Heteroarylamines into Pyridinium Salts and their Inter- and Intra-molecular Displacement
Katritzky Alan R.,Agha, Bushra J.,Awartani, Radi,Patel, Ranjan C.
, p. 2617 - 2621 (2007/10/02)
Heteroarylamines and the appropriate pyrylium salts give 1-heteroaryl-2-ethoxycarbonyl-4,6-diphenylpyridinium, and 1-(2-pyridyl)-2,6-diethoxycarbonyl-4-phenylpyridinium salts.Hydrolysis and decarboxylation afford 1-(2-pyridyl)-2,4-diphenyl- and 1-(2-pyridyl)-4-phenyl-pyridinium salts.Neither these, nor their 2,4,6-triphenyl analogues underwent smooth nucleophilic substitution. 1-Pyrimidin-2-yl- and 1-(4,6-dimethylpyrimidin-2-yl)-2-ethoxycarbonyl-4,6-diphenylpyridinium with ethanolic NaOEt smoothly formed the corresponding pyrimidin-2-ones via intramolecular attack.
Pyridinium Ylides Derived from Pyryliums and Amines and a Novel Rearrangement of 1-Vinyl-1,2-dihydropyridines
Katritzky, Alan R.,Chermprapai, Amornsri,Patel, Ranjan C.,Tarraga-Tomas, Alberto
, p. 492 - 497 (2007/10/02)
1-Benzyl-2,4-diphenylpyridiniums with benzaldehydes give oxazolopyridines which are dehydrated to 1-styryl derivatives.On pyrolysis the 1-styryl-1,2-dihydropyridine 21a gave 2,4,6-triphenylpyridine and m-chlorostyrene by a ring-enlargement-ring-contraction mechanism: this is a general reaction of 1-vinyl-1,2-dihydropyridines.
