16508-09-1Relevant articles and documents
Design, synthesis, and evaluation of a novel macrocyclic anti-EV71 agent
Li, Peng,Wu, Siqi,Xiao, Tianyichen,Li, Yunlong,Su, Zhiming,Wei, Wei,Hao, Fei,Hu, Guoping,Lin, Fusen,Chen, Xinsheng,Gu, Zhengxian,Lin, Tianwei,He, Haiying,Li, Jian,Chen, Shuhui
, (2020)
We describe here the design, synthesis, and evaluation of a macrocyclic peptidomimetic as a potent agent targeting enterovirus A71 (EV71). The compound has a 15-membered macrocyclic ring in a defined conformation. Yamaguchi esterification reaction was used to close the 15-membered macrocycle instead of the typical Ru-catalyzed ring-closing olefin metathesis reaction. The crystallographic characterization of the complex between this compound and its target, 3C protease from EV71, validated the design and paved the way for the generation of a new series of anti-EV71 agents.
Catalytic Enantioselective Synthesis of 3,4,5-Trisubstituted Isoxazoline N-Oxides and Regioselective Synthesis of 3,4,5-Trisubstituted Isoxazoles
Sahoo, Subas Chandra,Pan, Subhas Chandra
supporting information, p. 1385 - 1389 (2019/01/09)
An efficient catalytic asymmetric synthesis of 3,4,5-trisubstituted isoxazoline N-oxides and regioselective synthesis of 3,4,5-trisubstituted isoxazoles has been described. α-Nitrocinnamates and α-nitrobenzophenones were utilized as Michael acceptors resp
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions
Gagnot, Glwadys,Hervin, Vincent,Coutant, Eloi P.,Desmons, Sarah,Baatallah, Racha,Monnot, Victor,Janin, Yves L.
, p. 2846 - 2852 (2018/11/27)
We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)ethenes
Efimova,Ozerova,Novikova,Baichurin,Berestovitskaya
, p. 1496 - 1499 (2015/01/09)
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)-ethenes proceed via initial formation the aza-Michael product, are accompanied by liberation of nitroacetic ester (or nitroacetophenone), and result in N-aryl(het
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)ethenes
Efimova,Ozerova,Novikova,Baichurin,Berestovitskaya
, p. 1496 - 1499 (2015/02/19)
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)-ethenes proceed via initial formation the aza-Michael product, are accompanied by liberation of nitroacetic ester (or nitroacetophenone), and result in N-aryl(het
One-pot multifunctional catalysis with NNN-Pincer Zr-MOF: Zr base catalyzed condensation with Rh-catalyzed hydrogenation
Rasero-Almansa, Antonia M.,Corma, Avelino,Iglesias, Marta,Sánchez, Félix
, p. 3092 - 3100 (2013/10/21)
We describe the postsynthetic modification of Zr-based metal organic frameworks (MOFs) containing chiral NNN-pincer ligands based on aminopyridineimines, as well as the subsequent formation of (NNN)-M-Zr-MOF complexes (M=Rh, Ir). With these new multifunct
Domino reactions for the synthesis of various α-substituted nitro alkenes
Fioravanti, Stefania,Pellacani, Lucio,Vergari, Maria Cecilia
experimental part, p. 524 - 528 (2012/01/15)
Efficient one-pot methods for the synthesis of variously functionalised conjugated nitro alkenes have been reported. Despite the utility in different fields of these compounds, only a few multi-step syntheses have been reported in the literature, giving t
Nucleophilic addition to nitroacrylates: application towards the synthesis of 2,3-dehydroamino acids and 2,3-diamino acids
Lewandowska, Elzbieta,Wichlacz, Kinga,Sobczak, Adam J.
body text, p. 152 - 156 (2010/03/01)
The addition of the N-pronucleophiles to 2- or 3-nitro-2-alkenoates in the presence of base provided Michael addition products. In the case of 3-nitro compounds, reaction occurred via the formation of α-adducts and the subsequent elimination of nitrous ac
Iodobenzene diacetate/tetrabutylammonium iodide-induced aziridination of N-tosylimines with activated methylene compounds under mild conditions
Fan, Renhua,Ye, Yang
supporting information; scheme or table, p. 1526 - 1530 (2009/07/01)
Aziridination of N-tosylimines with activated methylene compounds induced by iodobenzene diacetate [PhI(OAc)2] and tetrabutylammonium bromide [Bu4NBr] afforded the corresponding 2,2-difunctionalized aziridines in good yields with the aid of a catalytic amount of base. The reaction is hypothesized to proceed via a tandem nucleophilic addition-oxidative cyclization pathway.
Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes
Versleijen, Jos P. G.,Van Leusen, Albert M.,Feringa, Ben L.
, p. 5803 - 5806 (2007/10/03)
The asymmetric copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Z-mixtures of α,β-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.'s. High enantioselectivities (e.e.'s up to 92%) w
