- A metal-free picolinamide assisted electrochemical ortho-trifluoromethylation of arylamines
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An eco-friendly and effective electrochemical process was developed for the ortho-trifluoromethylation of arylamines using CF3SO2Na as the trifluoromethyl source, affording the desired products in moderate to good yields with high regioselectivity under mild reaction conditions. Importantly, the requirement for both transition metals and oxidants utilized in previous methods were avoided. A radical mechanism was proposed on the basis of various control experiments.
- Wang, Kai,Hou, Jiahao,Wei, Tingting,Zhang, Changjun,Bai, Renren,Xie, Yuanyuan
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supporting information
(2020/12/21)
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- Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand
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Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.
- Tanaka, Kouichi,Miki, Takashi,Murata, Kunihiko,Yamaguchi, Ayumi,Kayaki, Yoshihito,Kuwata, Shigeki,Ikariya, Takao,Watanabe, Masahito
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p. 10962 - 10977
(2019/09/03)
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- Iron-catalyzed: Ortho trifluoromethylation of anilines via picolinamide assisted photoinduced C-H functionalization
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A convenient, oxidant-free protocol was developed for the ortho trifluoromethylation of aniline via picolinamide assisted Fe-promoted C-H functionalization under ultraviolet irradiation. In this transformation acetone essentially acted as both a solvent to dissolve reactants and a low-cost radical initiator to efficiently generate a CF3 radical from Langlois' reagent. A broad substrate scope was tolerated and picolinamide bearing strong electron withdrawing groups also could be transformed into the corresponding products with acceptable yields. Furthermore, the value of this method has been highlighted via the efficient synthesis of the nonsteroidal anti-inflammatory drug floctafenine.
- Xia, Chengcai,Wang, Kai,Wang, Guodong,Duan, Guiyun
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supporting information
p. 2214 - 2218
(2018/04/05)
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- AMINONAPTHOQUINONE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR BLOCKING UBIQUITINATION-PROTEASOME SYSTEM IN DISEASES
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The invention relates to new compounds with low cytotoxicity for blocking the ubiquitination- proteasome system in diseases. Accordingly, these compounds can be used in treatment of disorders including, but not limited to, cancers, neurodegenerative diseases, inflammatory disorders, autoimmune disorders and metabolic disorders.
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Paragraph 00200
(2017/02/09)
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- Highly efficient aerobic epoxidation of cyclic olefins in mild conditions by a novel binuclear manganese(II) complex containing N-(4-nitrophenyl)picolinamide ligand
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A novel binuclear Mn(II) complex based on a para-nitro substituted amidic ligand (N-(4-nitrophenyl)picolinamide) has been synthesized and characterized by X-ray crystallography. This complex shows a high degree of conversion and epoxide selectivity in Mukaiyama aerobic epoxidation reactions of cyclic olefins in mild conditions.
- Bagherzadeh, Mojtaba,Ghanbarpour, Alireza,Khavasi, Hamid Reza
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supporting information
p. 72 - 75
(2015/04/27)
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- Glutamate receptor photomodulators
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The present invention relates to the discovery of particular aromatic compounds of formula (1), possessing activity as modulators of metabotropic glutamate receptors (mGIuR) whose modulatory activity on the receptor may be controlled by irradiation with suitable light resulting in the optical control of receptor biological function, to the use of said compounds as a medicament, and to pharmaceutical compositions comprising said compounds of formula (1).
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Paragraph 0111-0114; 0121-0122
(2015/04/15)
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- N-picolinamides as ligands for Ullmann-type homocoupling reactions
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The use of N-phenylpicolinamide (NPPA) as a ligand in Ullmann-type homocoupling reactions of aryl iodides and bromides in common solvents, such as DMF and MeCN has been successfully demonstrated at room temperature. In addition, this work provided the first example of the homocoupling of an aryl chloride at 82 °C, which is a relatively low temperature when compared to regular Ullmann reaction temperatures. Also, NPPA was successfully employed in base-and heat free Suzuki reactions, including electron rich and poor aryl halides with heteroarylboronic acids in moderate yields.
- Damkaci, Fehmi,Altay, Esra,Waldron, Matthew,Knopp, Michael A.,Snow, David,Massaro, Nicholas
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supporting information
p. 690 - 693
(2014/01/23)
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- Reaction of N-fluoropyridinium fluoride with isonitriles and diazo compounds: A one-pot synthesis of (pyridin-2-yl)-1H-1,2,3-triazoles
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Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles and diazo compounds led to the formation of the corresponding (pyridine-2-yl)-1H-1,2,3-triazoles in good yields (37-59%). Best outcome was consistently achieved with bo
- Kiselyov, Alexander S.
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p. 2631 - 2634
(2007/10/03)
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- Reaction of N-fluoropyridinium fluoride with isonitriles: A convenient route to picolinamides
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Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles led to the formation of the corresponding picolinamides in good yields. A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline carboxylic acid. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.
- Kiselyov, Alexander S.
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p. 2279 - 2282
(2007/10/03)
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- Reaction of N-fluoropyridinium fluoride with isonitriles and TMSN 3: A convenient one-pot synthesis of tetrazol-5-yl pyridines
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Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles and TMSN3 led to the formation of the corresponding tetrazol-5-yl pyridines in good yields (37-84%). A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.
- Kiselyov, Alexander S.
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p. 4851 - 4854
(2007/10/03)
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- Potential Acyl-transfer Agents. Reactions of N-Acyl-2-pyridinecarboxamides with Nucleophiles
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A fast reaction is obserwed between a series of N-acyl-2-pyridinecarboxamides and cyclopentylamine or pyrrolidine.Most of the acylamides react exclusively at the pyridine-2-carbonyl group.The selectivity of these reactions is explained by the reaction of the pyridine-nitrogen as a base towards the external nucleophile in a five-ring transition state.The acylamides undergo slow reactions with 4-methylaniline, methanol or water.Several reaction paths are observed with these less reactive nucleophiles.An intramolecular acyl group transfer prior to the reaction with an external nucleophile is indicated for three of the N-acylamides which have an N,N-dialkylamino substituent in the pyridine-4-position.Nucleophilic attack occurs predominantly at the N-acyl group of these three compounds which are moderately active acyl-transfer agents.
- Morkved, Eva H.,Cronyn, Marshall W.
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p. 381 - 388
(2007/10/02)
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