17259-54-0Relevant academic research and scientific papers
Magnesiate-Utilized/Benzyne-Mediated Approach to Indenopyridones from 2-Pyridones: An Attempt to Synthesize the Indenopyridine Core of Haouamine
Idzik, Tomasz J.,Borzyszkowska-Ledwig, Aleksandra,Struk, ?ukasz,So?nicki, Jacek G.
supporting information, p. 9667 - 9671 (2019/11/29)
An efficient, short-staged synthesis of cis-fused indeno[2,1-b]- and indeno[1,2-c]pyridin-2-ones, starting from 2-pyridones, using magnesiates of type R3MgLi as nucleophilic and deprotonation agents, mediated by benzyne generated in situ, under optimized conditions, is described. Following the developed protocol, rare C4a-arylsubstituted indeno[2,1-b]pyridones, resembling the core of haouamine, were obtained. The protocol offering the one-pot synthesis directly from 2-pyridone is also described.
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
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.).
Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides
Maity, Saurabh,Das, Debapratim,Sarkar, Souradip,Samanta, Rajarshi
supporting information, p. 5167 - 5171 (2018/09/13)
A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.
Synthesis of: N -alkylated 2-pyridones through Pummerer type reactions of activated sulfoxides and 2-fluoropyridine derivatives
Hu, Gang,Xu, Jiaxi,Li, Pingfan
, p. 4151 - 4158 (2018/06/12)
N-Alkylated 2-pyridone products were obtained in good to excellent yields through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride activated sulfoxides and 2-fluoropyridine derivatives, followed by hydrolysis. This is a rare case that uses 2-fluoropyridine as a nucleophile in Pummerer type reactions.
Copper-catalyzed olefinic C-H difluoroacetylation of enamides
Caillot, Gilles,Dufour, Jérémy,Belhomme, Marie-Charlotte,Poisson, Thomas,Grimaud, Laurence,Pannecoucke, Xavier,Gillaizeau, Isabelle
supporting information, p. 5887 - 5890 (2014/05/20)
Copper-catalyzed olefinic difluoroacetylation of enamides via direct C-H bond functionalization using BrCF2CO2Et is reported for the first time. It constitutes an efficient radical-free method for the regioselective synthesis of β-di
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.
