- Direct Amidation of Carboxylic Acids with Nitroarenes
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N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium salt for one-pot amidation, without the need for isolation of the corresponding synthetic intermediates. Furthermore, the ease of preparation and workup allow the quick and efficient synthesis of a wide range of N-aryl amides, including several amide-based druglike and agrochemical molecules.
- Wang, Shao-Peng,Cheung, Chi Wai,Ma, Jun-An
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p. 13922 - 13934
(2019/11/03)
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- Selective amidation of unprotected amino alcohols using surfactant-in-water technology: A highly desirable alternative to reprotoxic polar aprotic solvents
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A general selective and environmentally friendly method for the formation of amide bonds using a surfactant in water as medium is described. The use of readily available 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide (EDC) and hydroxybenzotriazol (HOBt)
- Parmentier, Michael,Wagner, Mona K.,Magra, Kevin,Gallou, Fabrice
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supporting information
p. 1104 - 1107
(2017/01/16)
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- Sulfate Radical Anion (SO4?-) Mediated C(sp3)-H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles
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A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C(sp3)-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.
- Laha, Joydev K.,Tummalapalli, K. S. Satyanarayana,Nair, Akshay,Patel, Nidhi
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p. 11351 - 11359
(2015/12/01)
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- Highly efficient synthesis of fused bicyclic 2,3-diaryl-pyrimidin-4(3H)-ones via Lewis acid assisted cyclization reaction
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An expedient one-pot synthesis of fused bicyclic 2,3-diaryl-pyrimidin-4(3H)-ones from three readily available components is described. The key step is a Lewis acid assisted cyclization reaction.
- Yang, Kunyong,He, Xiaohui,Choi, Ha-soon,Wang, Zhicheng,Woodmansee, David H.,Liu, Hong
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p. 1725 - 1728
(2008/09/17)
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- AZOLOPYRIMIDINES AS INHIBITORS OF CANNABINOID 1 ACTIVITY
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The invention provides compounds of formula (Ia), (Ic), (Ig) and (Ik), pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of Cannabinoid Receptor 1 (CB1).
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Page/Page column 45-46; 63-64; 65; 76
(2008/06/13)
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