- Chemoselective reduction of α,β-unsaturated carbonyl compounds in the presence of CuPd alloy nanoparticles decorated on mesoporous graphitic carbon nitride as highly efficient catalyst
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Herein, we reported reductions of acid, amide, ester and ketone groups with selectivity (>99%) by the catalytic transfer hydrogenation of with CuPd alloy nanoparticles (NPs) decorated on mesoporous graphitic carbon nitride (Cu50Pd50/mpg-C3N4) catalyst under mild conditions in a water/methanol mixture. CuPd alloy NPs were synthesized by the co-reduction of palladium (II) acetylacetonate and copper(II) acetylacetonate in oleylamine (OAm) solution by the reduction of morpholine-borane solution and then assembled on mpg-C3N4 via liquid phase self‐assembly method. The α, β-unsaturated carbonyl compounds were obtained from the condensation reaction of the benzaldehyde derivatives with acetone derivatives. Cu50Pd50/mpg-C3N4 nanocatalyst was characterized by TEM, XRD, XPS, BET and ICP‐MS. Cu50Pd50/mpg-C3N4 nanocatalyst is highly active catalyst for the reduction of various organic groups and converted to high yield and 99% selectivity. The superior Cu50Pd50/mpg-C3N4 nanocatalyst is highly efficient and reusable catalyst which is reuse after 5 cycle with 98% conversion.
- Bayrak, Cetin,Menzek, Abdullah,Sevim, Melike
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- Palladium-Catalyzed Carbonylative Synthesis of α,β-Unsaturated Amides from Styrenes and Nitroarenes
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A procedure on palladium-catalyzed selective aminocarbonylation of styrenes with nitroarenes for the synthesis of α,β-unsaturated amides has been developed. A range of substituted α,β-unsaturated amides were synthesized in moderate to good yields. Interestingly, nitroarenes act as both a nitrogen source and oxidant, and Mo(CO)6 acts as a solid CO source and reductant in this catalytic system.
- Peng, Jin-Bao,Geng, Hui-Qing,Li, Da,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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supporting information
p. 4988 - 4993
(2018/08/24)
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- Boronic acid-DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
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Arylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) cooperatively catalyse the dehydrative condensation reaction between carboxylic acids and amines to give the corresponding amides under azeotropic reflux conditions. This cooperative use is much more effective than their individual use as catalysts, and chemoselectively promotes the amide condensation of (poly)conjugated carboxylic acids. The present method is practical and scalable, and has been applied to the synthesis of sitagliptin and a drug candidate.
- Ishihara, Kazuaki,Lu, Yanhui
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p. 1276 - 1280
(2016/02/05)
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- Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support
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A highly improved and green methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. The scope of this method is exemplified by the use of several aliphatic, aromatic, unsaturated and fatty acids. The reaction is also applied to different primary and secondary amines. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. Several experiments to illustrate the selectivity of this methodology were also carried out with several more functionalized acids and amines. This approach is a substantial improvement over other previously described methods in amide synthesis.
- Ojeda-Porras, Andrea,Hernández-Santana, Alejandra,Gamba-Sánchez, Diego
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supporting information
p. 3157 - 3163
(2015/05/27)
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- TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide
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A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.
- Song, Xian-Rong,Song, Bo,Qiu, Yi-Feng,Han, Ya-Ping,Qiu, Zi-Hang,Hao, Xin-Hua,Liu, Xue-Yuan,Liang, Yong-Min
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p. 7616 - 7625
(2014/09/16)
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- Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)
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A new method is described for the preparation of esters and amides promoted by TAPC from carboxylic acids using a solvent-free grinding technique. The solvent-free N-formylation of amines is also reported.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Targhan, Homa,Sheikh Arabi, Mehdi
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supporting information
p. 5064 - 5068
(2013/09/02)
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- Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors
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Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.
- Shi, Zhi-Hao,Li, Nian-Guang,Shi, Qian-Ping,Tang, Hao,Tang, Yu-Ping,Li, Wei,Yin, Lian,Yang, Jian-Ping,Duan, Jin-Ao
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p. 1206 - 1211
(2013/03/14)
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- Phosphine-based redox catalysis in the direct traceless staudinger ligation of carboxylic acids and azides
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Redox catalysis: Aryl amides, imides, lactams, and dipeptides are obtained through a direct Staudinger ligation mediated by phosphine-based redox catalysis (see scheme). Mechanistic studies indicate the involvement of a phosphonium carboxylate intermediate that leads to a 1,3-acyl migration and thus results in C-N bond formation. Copyright
- Kosal, Andrew D.,Wilson, Erin E.,Ashfeld, Brandon L.
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supporting information
p. 12036 - 12040
(2013/01/16)
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- SmI3-catalyzed addition of amines to α,β-unsaturated N-acylbenzotriazoles
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The addition of amines to α,β-unsaturated N-acylbenzotriazoles could be catalyzed by samarium triiodide (SmI3) at ambient temperature. α,β-Unsaturated aliphatic N-acylbenzotriazoles afforded bis-addition products (β-amino amides), whereas N-cinnamoylbenzo
- Wang, Xiaoxia,He, Liang,Li, Zhifang,Wang, Wencun,Liu, Junhua
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experimental part
p. 819 - 829
(2009/08/08)
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- 2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE
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The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein RA1, RA2, RA3, RA4, RB1, RB2, RNA, RNB, and X? are as defined herein: The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.
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Page/Page column 27; 46
(2009/10/06)
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- New procedure for the total synthesis of cilostamide
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An efficient route to synthesise a wide range of N,N-R,R-4-(2-oxo-1,2- dihydroquinolin-6-yloxy)butanamide, specially Cilostamide (R = methyl and R = cyclohexyl), one of the most selective inhibitors of phosphodiesterase3 (PDE3) enzyme, from 5-methoxy-2-ni
- Seyedi, Seyed Mohammad,Sadeghian, Hamid,Arghiani, Zahra
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experimental part
p. 183 - 186
(2009/04/06)
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- Photochemical debromination of vic-dibromides
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Photochemical debromination of dibromohydro cinnamamides gave the carbon-carbon double bond compounds.
- Aruna,Kalyanakumar,Ramakrishnan
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p. 3125 - 3130
(2007/10/03)
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