92444-98-9Relevant academic research and scientific papers
Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones
Chantarojsiri, Teera,Kittikool, Tanakorn,Phakdeeyothin, Kunita,Yotphan, Sirilata
supporting information, p. 3071 - 3078 (2021/07/22)
A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.
Iron-Catalyzed Reactions of 2-Pyridone Derivatives: 1,6-Addition and Formal Ring Opening/Cross Coupling
Huang, Lin,Gu, Yiting,Fürstner, Alois
, p. 4017 - 4023 (2019/08/07)
In the presence of simple iron salts, 2-pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6-addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non-thermodynamic Z,E-configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element.
Catalytic O- to N-Alkyl Migratory Rearrangement: Transition Metal-Free Direct and Tandem Routes to N-Alkylated Pyridones and Benzothiazolones
Mishra, Abhishek Kumar,Morgon, Nelson Henrique,Sanyal, Suparna,Robinson de Souza, Aguinaldo,Biswas, Srijit
, p. 3930 - 3939 (2018/09/14)
The present study reports the synthesis of N-alkylated pyridones and benzothiazolones via O- to N-alkyl group migration under transition metal-free TfOH-catalyzed reaction conditions for the first time, to the best of our knowledge. Primary as well as secondary alkyl groups smoothly migrate under the present reaction conditions. Moreover, a minor modification of the protocol used in this study is found to be applicable for an entirely new tandem synthesis of 2-alkoxy-N-heterocycles from the simplest starting materials in a solvent-free reaction conditions. Density Functional Theory (DFT) calculation identifies the energy species associated with the rearrangement, whereas, mechanistic experiments explore the role of the catalyst as the alkyl group transfer mediator. (Figure presented.).
Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides
Feng, Bin,Li, Yang,Li, Huan,Zhang, Xu,Xie, Huamei,Cao, Hongen,Yu, Lei,Xu, Qing
, p. 6769 - 6775 (2018/05/29)
A specific N-alkylation of 2-hydroxypyridines is achieved by reacting with organohalides under catalyst- and base-free conditions. The observed HX-facilitated conversion of pyridyl ether intermediates to 2-pyridone products may account for the success and
Addition of novel benzylmagnesium “ate” complexes of BnR2MgLi type to 2-(thio)pyridones and related compounds
So?nicki, Jacek G.,Idzik, Tomasz,Borzyszkowska, Aleksandra,Wróblewski, Emil,Maciejewska, Gabriela,Struk, ?ukasz
supporting information, p. 481 - 493 (2017/01/13)
Novel benzylation reagents BnR2MgLi were obtained by mixing benzylmagnesium chloride (BnMgCl) and appropriate organolithium compounds (RLi). As BnR2MgLi complexes are more nucleophilic than the parent Grignard compound they enabled regioselective C6-addition to electrophilic N-substituted 2-(thio)-pyridones and C4-addition to poorly reactive NH 2-(thio)pyridones in high and good yields, respectively. Thus, the application of these new reagents in efficient synthesis of 6-benzyl-3,6-dihydro- and 4-benzyl-3,4-dihydropyridin-2(1H)-ones is described. The prospect of wider application of BnR2MgLi in 1,4-addition to other electrophiles, comprising six-membered α,β-unsaturated systems is also presented.
ANTI-FIBROTIC PYRIDINONES
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Paragraph 0665; 0666; 0668, (2015/11/02)
This application relates to polycyclic compounds with a pyridinone or pyridinone derivative core including, substituted pyridinones, 5,6- and 6,6- bicyclic heterocycles and substituted pyridine-thiones. This application also discloses methods of preparing these polycyclic compounds, pharmaceutical compositions and medicaments comprising said compounds and methods to treat, prevent or diagnose diseases, disorders or conditions associated with fibrosis.
ANTI-FIBROTIC PYRIDINONES
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Paragraph 0872, (2014/04/17)
Disclosed are pyridinone compounds, method for preparing these compounds, and methods for treating fibrotic disorders.
Preparation of N-alkyl 2-pyridones via a lithium iodide promoted oto N-alkyl migration: Scope and mechanism
Tasker, Sarah Z.,Bosscher, Michael A.,Shandro, Christina A.,Ryu, Keun Ah,Snapper, Gregory S.,Utter, Jarrad M.,Anderson, Carolyn E.,Lanni, Erica L.,Ellsworth, Bruce A.
, p. 8220 - 8230,11 (2020/10/15)
An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20-97% yield). This method has been shown to be intermolecular and requires heat and lithium cation to occur.
Synthesis of substituted N-benzyl pyridones via an O- To N-alkyl migration
Lanni, Erica L.,Bosscher, Michael A.,Ooms, Bartel D.,Shandro, Christina A.,Ellsworth, Bruce A.,Anderson, Carolyn E.
, p. 6425 - 6428 (2008/12/21)
(Chemical Equation Presented) A new LiI-promoted O- to N-alkyl migration has been developed for the conversion of O-alkylated 2-hydroxy pyridines, quinolines, and pyrimidines to the corresponding N-alkylated heterocycles in good to excellent yields (57-99%). This method serves as an efficient means for the preparation of N-benzyl pyridones, quinolones, and pyrimidones.
A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 12. A General Synthesis of 2-Chloropyridines and 2-Pyridons
Meth-Cohn, Otto,Westwood, Keith T.
, p. 1173 - 1182 (2007/10/02)
The Vilsmeier formylation of tertiary and secondary enamides leads to 2-pyridons and 2-chloropyridines, respectively.The reaction appears to be quite general allowing substitution in the 1-, 3-, 5-, or 6-position or combinations of these.The major limitation arises with enamides which are unsymmetrically substituted on the double bond with alkyl groups, when mixtures can result.Attempts to introduce a 4-substituent by a variation of the Vilsmeier reagent had limited success.
