130973-06-7Relevant articles and documents
Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
Yan, Yiyan,Xu, Xiaohe,Jie, Xiaokang,Cheng, Jingya,Bai, Renren,Shuai, Qi,Xie, Yuanyuan
supporting information, p. 2793 - 2796 (2018/06/25)
The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.
Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides
Maity, Rajib,Naskar, Sandip,Das, Indrajit
, p. 2114 - 2124 (2018/02/23)
Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C-C and C-S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out.
Palladium-Catalyzed Regioselective Hydroaminocarbonylation of Alkynes to α,β-Unsaturated Primary Amides with Ammonium Chloride
Ji, Xiaolei,Gao, Bao,Zhou, Xibing,Liu, Zongjian,Huang, Hanmin
, p. 10134 - 10141 (2018/07/09)
α,β-Unsaturated primary amides have found numerous applications in drug development, organic materials, and polymer sciences. However, the catalytic synthesis of α,β-unsaturated primary amides via carbonylation of alkynes has long been an elusive endeavor. Here, we report a novel palladium-catalyzed hydroaminocarbonylation of alkynes with NH4Cl as the amine source, enabling the highly chemo- and regioselective synthesis of α,β-unsaturated primary amides. A variety of alkynes, including aromatic alkynes, aliphatic alkynes, terminal alkynes, internal alkynes, as well as diynes with various functional groups, react well. The method turns the parasitic noncoordination ability of ammonium salts into a strategic advantage, enabling the gram-scale reaction to be performed in the presence of 0.05 mol % of catalyst with excellent selectivity.
Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives
Olawode, Emmanuel O.,Tandlich, Roman,Prinsloo, Earl,Isaacs, Michelle,Hoppe, Heinrich,Seldon, Ronnett,Warner, Digby F.,Steenkamp, Vanessa,Kaye, Perry T.
, p. 284 - 296 (2018/03/09)
Cinnamyl- and thiazole-based compounds have been shown to exhibit diverse medicinal properties and a series of twelve (E)-2-styrylthiazole and (E)-2-[(naphthalen-1-yl)vinyl]thiazole derivatives, which are conjugates of both systems and which satisfy the "Lipinski rule of 5", have been synthesised and subjected to in vitro biological screening. While insignificant inhibition (60-98% viability at 10 μM) of HeLa (cervical cancer) cells was noted, all five of the (E)-2-[naphthalen-1- yl)vinyl]thiazole derivatives proved remarkably active against SH-SY5Y (neuroblastoma) cells with IC50 values ranging from 2.09 to 8.64 μM. Two of the seven (E)-2-styrylthiazoles were found to be moderately active (with IC50 values of 10.8 and 11.7 mM), whereas the remaining five analogues exhibit significant proliferation of SH-SY5Y cells (with IC50 values of 180-1000 mM). The results warrant further studies on the effects of styrylthiazoles on the differentiation and extension of SH-SY5Y cells in order to assess their activity in neurological degenerative diseases.
The triflic acid-mediated cyclisation of N-benzyl-cinnamamides
King, Frank D.,Caddick, Stephen
, p. 487 - 491 (2013/07/27)
N-Benzyl-cinnamamides cyclise with triflic acid to form 5-aryl-benzazepinones and/or cinnamamides.
The acid-mediated ring opening/cyclisation reaction of N-benzyl-α- aryl-azetidinones
King, Frank D.,Caddick, Stephen
, p. 9350 - 9354 (2012/11/07)
N-Benzyl-4-aryl-azetidinones undergo ring opening with triflic acid to form N-benzyl-cinnamamides, which either undergo cyclisation to give 5-aryl-benzazepin-3-ones or N-debenzylation to give cinnamamides.
The acid-mediated ring opening reactions of α-aryl-lactams
King, Frank D.,Caddick, Stephen
supporting information; experimental part, p. 3244 - 3252 (2012/06/01)
4-Aryl-azetidin-2-ones (β-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl ex
Zinc-mediated facile synthesis of α,β-unsaturated primary amides
Feng, Sunlin,Zhang, Zhiying,Jiang, Shilei,Yu, Xiaochun
experimental part, p. 382 - 384 (2010/11/03)
A general method for the synthesis of α,β-unsaturated primary amides was achieved by an one-pot, triphenylphosphine-and zinc powder-promoted Wittig reaction of bromoacetamide and aldehydes under solvent-free conditions.
Synthesis, structure and quantitative structure-activity relationships of σ receptor ligands, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazines
Fujimura, Ken-Ichi,Matsumoto, Junzo,Niwa, Masashi,Kobayashi, Tadayuki,Kawashima, Yoichi,In, Yasuko,Ishida, Toshimasa
, p. 1675 - 1683 (2007/10/03)
A set of the title compounds having different substituents (R1, R2) on their phenyl groups was synthesized to find σ receptor binding affinity. Among the compounds, 2b (R1=R2=Cl) has the most potent σ1-binding activity, while 2a (R1=R2=H, SA4503) was most selective to σ1 over σ2 receptor. The crystal structures of 2a and 2b were shown, by X-ray crystallography, to be similar except for the one torsional angle of their propylene parts. Quantitative structure-activity relationship study suggested the affinity of the compounds to the σ1 receptor was dependent on the electronic feature, Swain-Lupton's R or S(π) that was derived by molecular orbital method, of R1 and R2.
A facile approach to arylacetaldehydes via polymeric palladium catalyst
Zhuangyu,Yi,Honwen,Tsi-yu
, p. 539 - 542 (2007/10/02)
Several arylacetaldehydes 5 were synthesized in moderate yields via Heck reaction of acrylamide (1) with substituted iodobenzenes 2 in the presence of the polymeric catalyst (P)-phenyl-(1,10-phenanthroline)-palladium(0) [(P)-ph-phen·Pd(0)] followed by Hofmann reaction and subsequent hydrolysis.
