18065-78-6Relevant articles and documents
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
Iron-catalyzed regioselective direct arylation at the C-3 position of N-alkyl-2-pyridone
Modak, Atanu,Rana, Sujoy,Maiti, Debabrata
, p. 296 - 303 (2016/09/09)
A number of pharmaceutical compounds possess an arylated 2-pyridone moiety. The existing reports using expensive starting materials and/or superstoichiometric metal salts have prompted us to explore a possible user-friendly method for their synthesis. In this report, we demonstrate an easy-to-handle reaction condition with an iron catalyst for the exclusive generation of C-3-arylated pyridone via C-H functionalization.
Value of zeolites in asymmetric induction during photocyclization of pyridones, cyclohexadienones and naphthalenones
Sivasubramanian, Karthikeyan,Kaanumalle, Lakshmi S.,Uppili, Sundararajan,Ramamurthy
, p. 1569 - 1576 (2008/02/05)
Two strategies, namely chiral inductor and chiral auxiliary approaches, have been examined within zeolites with the aim of achieving asymmetric induction during the photocyclization of cyclohexadienone, naphthalenone and pyridone derivatives. Within zeoli
N- vs. O-alkylation in the Mitsunobu reaction of 2-pyridone
Comins, Daniel L.,Jianhua, Gao
, p. 2819 - 2822 (2007/10/02)
An N- vs. O-alkylation study of 2-pyridone with various alcohols and solvents under Mitsunobu conditions was carried out.
Sodium mercury edetate dehydrogenation of N-aliphatic substituted 1,2,3,6-tetrahydropyridine derivatives
Mohrle,Ottersbach
, p. 109 - 115 (2007/10/02)
Hg(II)-edta dehydrogenation of N-aliphatic substituted Δ3-piperideine 1 leads to polymers. From 4 carrying a hydroxy neighbour group in the aliphatic side chain, it is possible to yield definite oxidation products - in dependence of nucleophiles present - mainly 4-substituted piperidone-2 derivatives 5 and 9-12. The oxidation of corresponding 4-hydroxy- (19) or 4-amino- (20, 21) piperidines gives the same spectrum of products. A mechanism for all the reactions is proposed.