238433-75-5Relevant academic research and scientific papers
Preparation of oxazolines and oxazoles via a PhI(OAc)2-promoted cyclization of N-propargylamides
Yi, Wei,Liu, Qing-Yun,Fang, Xing-Xiao,Lou, Sheng-Chun,Liu, Gong-Qing
, p. 7012 - 7018 (2018/10/20)
A metal-free cyclization of N-propargylamides for the synthesis of various oxazolines and oxazoles via a 5-exo-dig process is presented. Using (diacetoxyiodo)benzene (PIDA) as a reaction promoter and lithium iodide (LiI) as an iodine source, intramolecula
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.
supporting information, 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.
Safe and Fast Flow Synthesis of Functionalized Oxazoles with Molecular Oxygen in a Microstructured Reactor
Bay, Sarah,Baumeister, Tobias,Hashmi, A. Stephen K.,R?der, Thorsten
, p. 1297 - 1304 (2016/07/23)
The synthesis of hydroperoxymethyl oxazoles by oxidation of alkylideneoxazoles with molecular oxygen was implemented in a microstructured reactor for increased safety and larger-scale applications. Elaborate studies on the influence of pressure and temper
From propargylic amides to functionalized oxazoles: Domino gold catalysis/oxidation by dioxygen
Hashmi, A. Stephen K.,Blanco Jaimes, Maria Camila,Schuster, Andreas M.,Rominger, Frank
, p. 6394 - 6408 (2012/09/22)
A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. The hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride.
The synthesis and activity of oxazole and thiazole analogues of urocanic acid
Millan, David S.,Prager, Rolf H.,Brand, Catherine,Hart, Prue H.
, p. 811 - 816 (2007/10/03)
Direct exposure of human skin to sunlight leads to suppression of the immune system, believed to be mediated by urocanic acid. The synthesis of oxazole and thiazole analogues of urocanic acid is reported, as is their effect on biological markers of the hu
