- Catalytic O- to N-Alkyl Migratory Rearrangement: Transition Metal-Free Direct and Tandem Routes to N-Alkylated Pyridones and Benzothiazolones
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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.).
- Mishra, Abhishek Kumar,Morgon, Nelson Henrique,Sanyal, Suparna,Robinson de Souza, Aguinaldo,Biswas, Srijit
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p. 3930 - 3939
(2018/09/14)
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- Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides
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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
- Feng, Bin,Li, Yang,Li, Huan,Zhang, Xu,Xie, Huamei,Cao, Hongen,Yu, Lei,Xu, Qing
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p. 6769 - 6775
(2018/05/29)
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- Hilbert-Johnson reaction under high pressure: A facile preparation of 2-pyridones
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For the first time, a facile synthesis of 2-pyridones utilizing a classical Hilbert-Johnson reaction of 2-methoxypyridines with haloalkanes under high pressure has been achieved. The reactions were sensitive to steric hindrance of haloalkanes.
- Matsumoto, Kiyoshi,Ikemi, Yukio,Suda, Machiko,Iida, Hirokazu,Hamana, Hiroshi
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p. 187 - 190
(2008/03/12)
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- Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder. Synthesis and activity of functionalized glutaramides
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Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.
- Pryde, David C.,Maw, Graham N.,Planken, Simon,Platts, Michelle Y.,Sanderson, Vivienne,Corless, Martin,Stobie, Alan,Barber, Christopher G.,Russell, Rachel,Foster, Laura,Barker, Laura,Wayman, Christopher,Van Der Graaf, Piet,Stacey, Peter,Morren, Debbie,Kohl, Christopher,Beaumont, Kevin,Coggon, Sara,Tute, Michael
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p. 4409 - 4424
(2007/10/03)
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