- Cu-catalyzed cross-coupling of methyl ketones and pyridin-2-amines for the synthesis of N-(2-pyridyl)-α-ketoamides
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An efficient copper-catalyzed strategy for the synthesis of α-ketoamides via cross-coupling of methyl ketones and pyridin-2-amines is described. This transformation has provided a simple process for the formation of C?N and C=O bonds to prepare α-ketoamid
- Chen, Ali,Guo, Pengfeng,Lin, Haoming,Liu, Xiang,Rao, Chuixiong,Yang, Daji,Yu, Yue
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p. 417 - 421
(2020/11/30)
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- Copper(I)-catalysed aerobic oxidative selective cleavage of C[sbnd]C bond with DMAP: Facile access to N-substituted benzamides
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A base/DMAP system for efficient oxidative cleavage of C(CO)–C(alkyl) bond to generate N-substituted benzamides has been developed in the presence of copper(I) chloride. The usage of inexpensive copper catalyst, broad substrate scope, mild conditions make
- Ma, Haojie,Lu, Guoqiang,Han, Bo,Huang, Guosheng,Zhang, Yuqi,Wang, Ji-Jiang
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supporting information
(2021/06/15)
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- Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light
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A tandem cleavage of carbon-carbon and carbon-nitrogen bonds in imidazo[1,2-a]pyridines and imidazo[1,2-a]quinolines is reported in the presence of eosin Y and visible light. The ring opening occurs under ambient conditions through singlet oxygen insertio
- Jain, Nidhi,Kumar, Sharvan,Ritu,Sharma, Charu
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p. 2921 - 2928
(2020/04/28)
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- Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones: A Divergent Approach to 1,8-Naphthalimides, Biphenyl-2,2′-dicarboxamides, and N-Heterocyclic Amides
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We report here a simple and efficient copper catalyzed oxidative C-C bond cleavage of stable aromatic cyclic-fused and acyclic 1,2-diketones to deliver amides and imides in high yields. This newly developed protocol provides an excellent tool to transform structurally different 1,2-diketones into different products under the same reaction conditions. The key synthetic features of this methodology are the formation of 1,8-naphthalimides and biphenyl-2,2′-dicarboxamide motifs in high yields. The fluorescent studies of 1,8-naphthalimide derivatives were also carried out in order to show the potential application of these scaffolds.
- Sakhare, Priyanka R.,Subramanian, Parthasarathi,Kaliappan, Krishna P.
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p. 2112 - 2125
(2019/02/14)
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- Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
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A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
- Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
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p. 482 - 487
(2019/01/04)
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- Chemodivergent synthesis of: N -(pyridin-2-yl)amides and 3-bromoimidazo[1,2- a] pyridines from α-bromoketones and 2-aminopyridines
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N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C-C bond cleavage promoted by I2/s
- Liu, Yanpeng,Lu, Lixue,Zhou, Haipin,Xu, Feijie,Ma, Cong,Huang, Zhangjian,Xu, Jinyi,Xu, Shengtao
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p. 34671 - 34676
(2019/11/13)
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- Singlet oxygen mediated one pot synthesis of N-pyridinylamides via oxidative amidation of aryl alkyl ketones
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An environmental friendly, efficient protocol has been realized for the synthesis of N-pyridinylamides via copper catalyzed oxidative amidation of aryl alkyl ketones with 2-aminopyridines. This one pot protocol involves chemo selective cleavage of C (O)–C bond in the presence of singlet oxygen. The reaction conditions are simple, tolerates wide range of substrates and the products were formed in good to excellent yields. This method offers a moderate improvement over the earlier successful attempts in generating N-pyridinylamides.
- Sofi, Firdoos Ahmad,Sharma, Rohit,Kavyasree,Salim, Sumi Aisha,Wanjari, Pravin J.,Bharatam, Prasad V.
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supporting information
(2019/09/10)
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- Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants
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An efficient synthesis of a variety of pyridyl benzamides from 2-aminopyridines and nitroolefins is described. This rare-earth-metal-catalyzed reaction provides the corresponding products with broad substrate scope in moderate to excellent yields, in the absence of additives and external oxidants. Water is used as the source of the carbonyl oxygen atom in pyridyl benzamides. Furthermore, 2-substituted oxazolo[4,5-b]pyridines are formed in good yields under the standard conditions when 2-aminopyridin-3-ols are used as the substrates.
- Chen, Zhengwang,Wen, Xiaowei,Qian, Yiping,Liang, Pei,Liu, Botao,Ye, Min
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supporting information
p. 1247 - 1251
(2018/03/06)
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- Chemoselective acylation of primary amines and amides with potassium acyltrifluoroborates under acidic conditions
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Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and potassium acyltrifluoroborates promoted by simple chlorinating agents that proceeds rapidly in water. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations and can be applied to late-stage functionalizations.
- Galvez, Alberto Osuna,Schaack, Cedric P.,Noda, Hidetoshi,Bode, Jeffrey W.
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supporting information
p. 1826 - 1829
(2017/02/15)
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- Transformation of aldehydes or alcohols to amides at room temperature under aqueous conditions
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A novel and efficient method for the synthesis of amide has been developed. The reactions proceeded smoothly under aqueous conditions at room temperature and generated the corresponding products in good to excellent yields. It is worth noting that alkyl amines which did not react in known approaches are well tolerated in our system.
- Dong, Dao-Qing,Hao, Shuang-Hong,Zhang, Hui,Wang, Zu-Li
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p. 1597 - 1599
(2017/07/17)
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- Metal-free oxidative amidation of aldehydes with aminopyridines employing aqueous hydrogen peroxide
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The first metal free report on the amidation of aldehydes with aminopyridines was accomplished using simple aqueous hydrogen peroxide (aq. H2O2) as the oxidant. No catalysts or additives were needed for this transformation and the reaction proceeded in water, an environmentally benign reaction medium. Green oxidant and reaction conditions, and the ability to construct diverse N-(pyridin-2-yl)benzamide by this elegant method render it a practical alternative for the synthesis of these amides.
- Sankari Devi,Alanthadka, Anitha,Tamilselvi,Nagarajan, Subbiah,Sridharan, Vellaisamy,Maheswari, C. Uma
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supporting information
p. 8228 - 8231
(2016/09/09)
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- Microwave-assisted heteropolyanion-based ionic liquid promoted sustainable protocol to N-heteroaryl amides via N-directing dual catalyzed oxidative amidation of aldehydes
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A sustainable procedure for the synthesis of N-heteroaryl amides directly from oxidative amidation of aldehydes catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions has been reported. The transformation has proven to tolerate a wide range of aldehydes and amino heterocycles with different functional groups. Moderate to excellent yields, solvent-free media, operational simplicity and reusability of catalysts are the main highlights. Furthermore, the proposed N-directing dual-catalysis mechanistic pathway was briefly investigated in this report.
- Fu, Renzhong,Yang, Yang,Jin, Weihua,Gu, Hui,Zeng, Xiaojun,Chai, Wen,Ma, Yunsheng,Wang, Quan,Yi, Jun,Yuan, Rongxin
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p. 107699 - 107707
(2016/11/29)
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- Copper(i)-catalysed oxidative C-N coupling of 2-aminopyridine with terminal alkynes featuring a CC bond cleavage promoted by visible light
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Facile visible-light promoted copper-catalyzed aerobic oxidative C-N coupling between 2-aminopyridine and terminal alkynes at room temperature via CC triple bond cleavage is described. This reaction allows direct synthesis of biologically important pyridy
- Ragupathi, Ayyakkannu,Sagadevan, Arunachalam,Lin, Chun-Cheng,Hwu, Jih-Ru,Hwang, Kuo Chu
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supporting information
p. 11756 - 11759
(2016/10/07)
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- Copper-catalyzed highly efficient oxidative amidation of aldehydes with 2-aminopyridines in an aqueous micellar system
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An environmentally benign protocol for the synthesis of N-(pyridine-2-yl)amides from aldehydes and 2-aminopyridines has been developed under mild reaction conditions. This approach requires Cu(OTf)2 as a catalyst, and inexpensive molecular iodi
- Patel, Om P. S.,Anand, Devireddy,Maurya, Rahul K.,Yadav, Prem P.
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supporting information
p. 3728 - 3732
(2015/07/15)
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- Catalytic role of Cu(I) species in Cu2O/CuI supported on MWCNTs in the oxidative amidation of aryl aldehydes with 2-aminopyridines
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Cu2O and CuI were supported on multiwalled carbon nanotubes (MWCNTs) using a wet impregnation method, and the resulting materials were fully characterized by powder X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy with energy dispersive X-ray spectroscopy, transmission electron microscopy, and temperature-programmed desorption with ammonia analysis. The results of these experiments revealed that Cu2O and CuI were deposited on the MWCNTs in the cubic and γ phases, respectively. These results also showed that the Cu-containing MWCNTs exhibited weak to strong electron-accepting (Lewis acidic) properties. The catalytic activities of these materials were studied for the synthesis of biologically significant N-(pyridin-2-yl)benzamides via the oxidative amidation of aryl aldehydes with 2-aminopyridines. The yields of the products were in the range 50%-95% with 100% selectivity. Notably, the CuI/MWCNT catalyst was much more effective than the Cu2O/MWCNT catalyst with respect to the isolated yield of the product, although the latter of these two catalysts exhibited much better recyclability. A preferential interaction was observed between the polar nature of the acid-activated MWCNTs and the ionic Cu2O compared with covalent CuI. The differences in these interactions had a significant impact on the rate of the nucleophilic attack of the amino group of 2-aminopyridine substrate on the carbonyl group of the aryl aldehyde.
- Hareesh,Minchitha,Nagaraju,Kathyayini
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p. 1825 - 1836
(2015/11/17)
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- Cooperation of a Reductant and an Oxidant in One Pot to Synthesize Amides from Nitroarenes and Aldehydes
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The reductant zinc powder and the oxidant sodium chlorate were used together in an appropriate ratio in one pot under ambient conditions, to provide an environmentally friendly, effective, and convenient method for the synthesis of aromatic amides in good yields from nitroarenes and aldehydes in the green solvents alcohol and water under atmospheric conditions. The good results indicate that reductants and oxidants with opposing properties can not only be used together without any adverse effects, but also improve the reaction yield through their cooperation.
- Sheng, Guozhu,Wu, Xia,Cai, Xiuhua,Zhang, Wei
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p. 949 - 954
(2015/03/30)
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- ORGANIC MOLECULES FOR TERAHERTZ TAGGING APPLICATIONS
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The present invention discloses substituted heterocyclic compounds and /or aromatic compounds containing amide and/or urea groups exhibiting resonance in the range of 0.1- 10 THz. The invention also discloses binary molecular complexes based on the substituted heterocyclic compounds and/or aromatic compounds containing amide and/or urea groups of the present invention. The compounds and binary molecular complexes of the present invention have varying molecular mass and hydrogen bond strengths demonstrating several resonances below 10 THz. The compounds and binary molecular complexes of the present invention are customizable for various applications, such as authentication of a product.
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Page/Page column 14
(2015/07/23)
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- A one-pot copper catalyzed biomimetic route to n -heterocyclic amides from methyl ketones via oxidative c-c bond cleavage
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A direct one-pot Cu-catalyzed biomimetic oxidation of methyl ketones to pharmaceutically important N-heterocyclic amides is reported. The scope of the method is broad, scalable, and mild, and the reaction is tolerant with various acid, base sensitive functionalities with multiple heteroatoms and aryl halides. The extensive mechanistic studies suggest that this reaction follows the Luciferin-Luciferase-like pathway.
- Subramanian, Parthasarathi,Indu, Satrajit,Kaliappan, Krishna P.
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supporting information
p. 6212 - 6215
(2015/01/09)
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- Process for preparing arylamines
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The invention relates to a process for preparing arylamines or heteroarylamines or arylamides or heteroarylamides by cross-coupling of primary or secondary amines or amides with substituted aryl or heteroaryl compounds in the presence of a Br?nsted base a
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Page/Page column 5
(2008/06/13)
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- Synthesis of NCA [carbonyl-11C]amides by direct reaction of in situ generated [11C]carboxymagnesium halides with amines under microwave-enhanced conditions
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No-carrier-added (NCA) aromatic and aliphatic [carbonyl- 11C]amides were rapidly (11C]carboxymagnesium halides generated in situ from Grignard reagents and cyclotronproduced [11C]carbon dioxide. In this system cyclohexylcarboxymagnesium chloride (1b) is more reactive than 4-fluorophenylcarboxymagnesium bromide (2b) and primary amines (e.g. aniline, aminopyridines) far more reactive than secondary amines (e.g. 2-(methylamino)pyridine). The scope of the reaction was widened considerably by the application of microwaves, which allowed reactions to be carried out at much higher temperature than the boiling point of the solvent (i.e. tetrahydrofuran, b.p. 67°C). Copyright
- Lu, Shui-Yu,Hong, Jinsoo,Pike, Victor W.
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p. 1249 - 1259
(2007/10/03)
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