1044501-41-8Relevant academic research and scientific papers
Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst
Godha, Atul K.,Thiruvengadam, Jayaraman,Abhilash, Viswanadhan,Balgi, Prajwal,Narayanareddy,Vignesh, Kumaresan,Gadakh, Amol V.,Sathiyanarayanan,Ganesh, Sambasivam
supporting information, p. 16041 - 16045 (2019/10/28)
An environmentally benign, practically scalable and highly selective C-arylalkylation of active methylene compounds is developed using CTAB as the inverse phase transfer catalyst in water. The methodology developed is elaborated into the one-pot synthesis of quinoline derivatives and also applicable to the regioselective N-aralkyl of 2-pyridones.
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
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.
A process for preparing N - alkyl derivatives of green synthesis method
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Paragraph 0056; 0057; 0058, (2017/08/25)
The invention discloses a green synthetic method for preparation of N-alkyl pyridone. According to the method, a hydroxypyridine compound and alcohol undergo selective dehydration N-alkylation under the catalysis of a non-transition metal catalyst, wherein the non-transition metal catalyst is halogenated hydrocarbon; alcohol and the hydroxypyridine compound directly undergo N-selective dehydration under the catalysis of halogenated hydrocarbon so as to obtain an N-alkyl pyridone compound; the usage amount of the halogenated hydrocarbon is 5 to 50 mol%; reaction temperature is 100 to 180 DEG C; reaction time is 6 to 60 hours; and the byproduct is water. The method provided by the invention employs cheap, easily and widely available, stable and low-toxicity alcohol as an alkylating reagent and common halogenated hydrocarbon as the non-transition metal catalyst and directly synthesizes the N-alkyl pyridone compound through highly-selective dehydration N-alkylation without a solvent. The method has low requirements on reaction conditions, a wide application scope and certain research and industrial application prospects.
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.
