- POCl3 promoted metal-free synthesis of tertiary amides by coupling of carboxylic acids and N,N-disubstituted formamides
-
Herein we report a robust and synthetically useful catalyst-free amination methodology by the coupling of carboxylic acids and N-substituted formamides using POCl3 as a promoter. Versatile amides with a wide array of substituent groups were prepared within only 1 h in good to excellent yields. And even multi-substituted aromatic carboxylic acids could give the desired products with satisfactory results.
- Bi, Xiaojing,Li, Junchen,Shi, Enxue,Li, Yu,Liu, Ying,Wang, Hongmei,Xiao, Junhua
-
supporting information
p. 236 - 240
(2019/04/25)
-
- Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols and N-substituted Formamides Using a Co–Al Based Heterogeneous Catalyst
-
Present work reports the direct synthesis of amides from oxidative coupling of benzyl alcohols with various N-substituted formamides using a cobalt-hydrotalcite (Co-HT) derived catalyst. The Co-HT derived catalysts (Co-HT-2, Co-HT-3 and Co-HT-4 having Co2+/Al3+ molar ratio in the catalyst preparation mixture as 1/1, 2/1 and 3/1 respectively) were prepare following a co-precipitation method and characterized well by powder XRD, XPS, FEG-SEM, EDS, DTG–TGA, FT-IR and N2 physisorption measurements. A range of functional amides were obtained in good yields from oxidative coupling of various substituted benzyl alcohols and a range of N-substituted formamides using Co-HT-3 catalyst and oxidant TBHP. Mechanistic investigation suggests that the amidation reaction is associated with the formation and coupling of radical species. Furthermore, the Co-HT derived catalyst was easily recoverable and recyclable with retained high catalytic activity towards the oxidative coupling of benzyl alcohol with DMF. Graphical Abstract: [Figure not available: see fulltext.].
- Subhedar, Dnyaneshwar D.,Gupta, Shyam Sunder R.,Bhanage, Bhalchandra M.
-
p. 3102 - 3111
(2018/08/21)
-
- Oxidative amidation of benzaldehydes and benzylamines with: N -substituted formamides over a Co/Al hydrotalcite-derived catalyst
-
The present work describes a highly efficient synthetic strategy for amides via oxidative coupling of benzaldehydes or benzylamines with N-substituted formamides using a heterogeneous Co/Al hydrotalcite-derived catalyst in the presence of TBHP. A series of Co/Al hydrotalcite-derived catalysts (Cat-2, Cat-3, and Cat-4 with the Co2+/Al3+ molar ratio in the synthesis mixture as 1/1, 2/1 and 3/1) have been prepared by a simple co-precipitation method and characterized using powder XRD, XPS, FEG-SEM, EDS, FT-IR, DTG-TGA and N2 physical adsorption techniques. Among the as-prepared catalysts, Cat-3 exhibited excellent catalytic activity towards the direct amidation of benzaldehydes as well as benzylamines bearing various substituents into the corresponding amides at 100 °C using TBHP as an oxidant. The mechanistic investigation of the amidation reaction revealed that the reaction follows a radical pathway. Furthermore, the catalyst is easily separable and recyclable without considerable loss in catalytic activity.
- Gupta, Shyam Sunder R.,Nakhate, Akhil V.,Rasal, Kalidas B.,Deshmukh, Gunjan P.,Mannepalli, Lakshmi Kantam
-
p. 15268 - 15276
(2017/12/15)
-
- FeCl3 catalyzed amide compound synthesis method
-
The invention relates to an FeCl3 catalyzed amide compound synthesis method. According to the synthesis method, carboxylic acid and N-substituted formamide are employed to synthesize an amide compound under the catalysis of FeCl3. The synthesis method provided by the invention has the characteristics of mild conditions, high reaction efficiency, and wide applicability to substrates of different functional groups. The amide compound efficiently constructed by the invention is an important skeleton of many organic molecules, drugs, proteins and bioactive molecules. The synthesis method provided by the invention provides a widely applicable preparation method for synthesis of the compounds.
- -
-
Paragraph 0035; 0036; 0037; 0038; 0039
(2018/03/28)
-
- Synthesis method of amide aryl compound
-
The invention relates to a synthesis method of an amide aryl compounds. According to the method, Ru-(p-cymene) C12 is taken as a catalyst, K2S2O8 is taken as an oxidizing agent, Xantphos is taken as a ligand, one reactant (N, N-dialkyl formamide) is taken
- -
-
Paragraph 0050; 0051; 0052; 0053; 0054
(2017/04/19)
-
- Method for synthesizing phosphorus-oxychloride-promoted amide compound
-
The invention relates to a method for synthesizing a phosphorus-oxychloride-promoted amide compound. The synthesizing method includes the steps that carboxylic acid serves as one reactant, another reactant (N,N-dialkyl methanamide) serves as a solvent, one equivalent of phosphorus oxychloride is added, and the amide compound is prepared. The reaction substrates are low in price and easy to get, the nature is stable, toxicity is small, the reaction speed is high, conditions are moderate, and the reaction substrates can be widely applied to substrates with different functional groups. The efficiently-constructed amide compound is an important molecular skeleton for many medicines, bioactive molecules and natural products, and the synthesizing method is a widely-applicable preparing method for synthesizing the compound.
- -
-
Paragraph 0055; 0056; 0057; 0058; 0059
(2017/01/26)
-
- Ru-catalyzed direct amidation of carboxylic acids with N-substituted formamides
-
The direct amidation of carboxylic acids with N-substituted formamides has been accomplished via ruthenium catalysis. In the presence of ruthenium catalyst, a versatile range of carboxylic acids and N-substituted formamides undergoes amidation reaction to produce synthetically useful amides in good yields. C[dbnd]O in amide product came from benzoic acid but not N-substituted formamides, and which was confirmed by Isotope experiment.
- Bi, Xiaojing,Li, Junchen,Shi, Enxue,Wang, Hongmei,Gao, Runli,Xiao, Junhua
-
p. 8210 - 8214
(2016/11/23)
-
- Easy access to amides through aldehydic C-H bond functionalization catalyzed by heterogeneous Co-based catalysts
-
A novel synthesis strategy for amides by oxidative amidation of aldehydes is developed using a heterogeneous Co-based catalyst. The Co composite was prepared by simple pyrolysis of a Co-containing MOF, to obtain well-dispersed Co nanoparticles enclosed by carbonized organic ligands. The catalysts were characterized by powder X-ray diffraction (PXRD), N2 physical adsorption, atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), and X-ray photoelectron spectroscopy (XPS). The small Co nanoparticles embedded in the N-doped carbons were highly dispersed with an average size of ca. 7 nm. The Co@C-N materials exhibited significantly enhanced catalytic activity in the oxidative amidation of aldehydes in comparison to those of commercial sources. A series of amides can be easily obtained in good to excellent yields. It was found that the reaction proceeded via radicals under mild conditions, and the carbonyl group in the amide product was from the aldehyde. Moreover, the catalyst could be easily separated by using an external magnetic field and reused several times without significant loss in catalytic efficiency under the investigated conditions. (Chemical Equation Presented).
- Bai, Cuihua,Yao, Xianfang,Li, Yingwei
-
p. 884 - 891
(2015/02/19)
-
- Copper-catalyzed amide bond formation from formamides and carboxylic acids
-
A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.
- Liu, Hong-Qiang,Liu, Jun,Zhang, Yang-Hui,Shao, Chang-Dong,Yu, Jing-Xun
-
-
- Copper-catalyzed synthesis of α,β-unsaturated acylamides via direct amidation from cinnamic acids and N-substituted formamides
-
A highly effective synthesis of α,β-unsaturated acylamides is reported for the first time via copper-catalyzed direct amidation between readily available cinnamic acids and N-substituted formamides. The protocol was easily accessible and practical.
- Yan, Hong,Yang, Hailong,Lu, Linhua,Liu, Defu,Rong, Guangwei,Mao, Jincheng
-
p. 7258 - 7263
(2013/08/23)
-
- ANTHRANILAMIDE INHIBITORS OF AURORA KINASE
-
The present invention relates to a compound represented by the following formula: or a pharmaceutically acceptable salt thereof; where R1, R2, R3, R4, r and s are as previously defined. Compounds of the present invention are useful in the treatment of diseases associated with Aurora kinase activity such as cancer.
- -
-
Page/Page column 13
(2008/12/07)
-
- [3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy]-pyridine, pyrimidine and benzene derivatives as α1 -adrenoceptor antagonists
-
The present invention relates to novel α 1 -adrenoceptor antagonists of Formula I: STR1 in which: p is 0 or 1;t is 0, 1 or 2;X is O, S or NR 6 (in which R 6 is hydro or (C 1-6)alkyl);Y and Z are independently CH or N;R 1 is hydro, hydroxy, halo, nitro, amino, cyano, (C 1-4)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C 1-6)alkyl, (C 3-6)cycloalkyl, (C 3-6)cycloalkyl (C 1-4)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl (C 1-4)alkyl, heteroaryl (C 1-4)alkyl, (C 1-6)alkyloxy, (C 3-6)cycloalkyloxy, (C 3-6)cycloalkyl (C 1-4)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl (C 1-4)alkyloxy or heteroaryl (C 1-4)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano);R 2 is hydro, hydroxy, halo, cyano, (C 1-6)alkyl or (C 1-6)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms);R 3 is -C (O)R 7 (wherein R 7 is (C 1-6)alkyl, (C 3-6)cycloalkyl, di(C 1-4)alkylamino, N-(C 1-4)alkyl-N-(C 1-4)alkyloxyamino, (C 1-4)alkyl((C 1-4)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl);R 4 is halo, hydroxy, cyano, (C 1-6)alkyl or (C 1-6)alkyloxy; andR 5 is (C 1-6)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.
- -
-
-
- N-Arylpiperazinyl-N'-propylamino derivatives of heteroaryl amides as functional uroselective α1-adrenoceptor antagonists
-
Novel arylpiperazines were identified as α1-adrenoceptor (AR) subtype- selective antagonists by functional in vitro screening. 3-[4-(ortho- Substituted phenyl)piperazin-1:yl]propylamines were derivatized with N,N- dimethyl anthranilamides, nicotinamides, as well as carboxamides of quinoline, 1,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4- b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta were used as a 'negative screen' for the test antagonists. Binding to α1-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g. 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the α1-AR subtype prevalent in the human lower urinary tract (pA2 values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the α(1D)-AR.
- Elworthy, Todd R.,Ford, Anthony P. D. W.,Bantle, Gary W.,Morgans Jr., David J.,Ozer, Rachel S.,Palmer, Wylie S.,Repke, David B.,Romero, Magarita,Sandoval, Leticia,Sjogren, Eric B.,Talamás, Francisco X.,Vazquez, Alfredo,Wu, Helen,Arredondo, Nicolas F.,Blue Jr., David R.,DeSousa, Andrea,Gross, Lisa M.,Kava, M. Shannon,Lesnick, John D.,Vimont, Rachel L.,Williams, Timothy J.,Zhu, Quan-Ming,Pfister, Jürg R.,Clarke, David E.
-
p. 2674 - 2687
(2007/10/03)
-
- Trapping of translocated radicals by tetrathiafulvalene radical cation
-
Aryl radicals are generated by electron transfer from tetrathiafulvalene to arenediazonium salts.The aryl radicals are translocated into alkyl radicals which undergo a C-S or C-C bond formation to tetrathiafulvalene radical cation, depending on the nucleophilicity/electrophilicity of the translocated carbon radical.
- Murphy, John A.,Roome, Stephen J.
-
p. 1349 - 1358
(2007/10/02)
-
- INVESTIGATIONS ON N,N-DIALKYLBENZAMIDES BY NMR SPECTROSCOPY. PART IV. COMPARISON OF BARRIERS TO ROTATION ABOUT THE AMINE C-N BOND IN ORTHO-SUBSTITUTED N,N-DIMETHYL-AND N,N-DIETHYLBENZAMIDES
-
The barriers to rotation about the amide C-N bond in a series of ortho-substituted N,N-dimethyl and N,N-diethylbenzamides have been compared.It has been stated that for most of substituents, namely CH3, Cl, Br, I and NO2, the rates of rotation in both series of compounds are identical within the accuracy of measurement (kEt/kMe ca.1).The remaining compounds (F, CN, CH3) show a higher rate of rotation in the series of diethylbenzamides (kEt/kMe ca.1,5).An exception are the OH derivatives in which the internal H-bond is present and because of that the barrier to rotation is lowered and the kEt/kMe ratio raised up to 2.3.
- Gryf-Keller, Adam,Terpinski, Jacek,Zajaczkowska-Terpinska, Ewa
-
p. 429 - 434
(2007/10/02)
-