32418-03-4Relevant academic research and scientific papers
Effective C5-Arylation of Peptide-Integrated Oxazoles: Almazole D
Oberheide, Ansgar,Arndt, Hans-Dieter
, p. 1132 - 1136 (2020/12/22)
An efficient functionalization approach of oxazoles by using Pd-catalyzed cross-coupling reactions is reported. Oxazolone formation and subsequent sulfamoylation in situ are facilitated by employing N,N-diethylsulfamoyl imidazolium triflate. Cross-couplings provide both oxazole-arenes and oxazole-heteroarenes and were compatible with sensitive and epimerization-prone substrates, as exemplified by the total synthesis of the natural product almazole D. (Figure presented.).
Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis
Chatterjee, Tanmay,Cho, Ji Young,Cho, Eun Jin
, p. 6995 - 7000 (2016/08/30)
A simple and practical method for the synthesis of substituted oxazoles has been developed using readily available α-bromoketones and benzylamines by visible-light photocatalysis at room temperature. The process, which requires 1 mol % of [Ru(bpy)3]Cl2 photocatalyst with K3PO4 and CCl3Br, is effective for accessing a variety of valuable oxazole compounds. The synthetic utility of our protocol was also demonstrated by preparing a natural product, texaline.
Structure-activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors
Im, Isak,Lee, Eui Seung,Choi, Soo Jeong,Lee, Ju-Yeon,Kim, Yong-Chul
scheme or table, p. 3632 - 3636 (2010/03/24)
Human rhinovirus 3C protease (HRV 3Cpro) is known to be a promising target for development of therapeutic agents against the common cold because of the importance of the protease in viral replication as well as its expression in a large number of serotypes. To explore non-peptidic inhibitors of HRV 3Cpro, a series of novel heteroaromatic esters was synthesized and evaluated for inhibitory activity against HRV 3Cpro, to determine the structure-activity relationships. The most potent inhibitor, 7, with a 5-bromopyridinyl group, had an IC50 value of 80 nM. In addition, the binding mode of a novel analog, 19, with the 4-hydroxyquinolinone moiety, was explored by molecular docking, suggesting a new interaction in the S1 pocket.
Convenient preparation of substituted 5-aminooxazoles via a microwave-assisted Cornforth rearrangement
Nolt, M. Brad,Smiley, Mark A.,Varga, Sandor L.,McClain, Ray T.,Wolkenberg, Scott E.,Lindsley, Craig W.
, p. 4698 - 4704 (2007/10/03)
The preparation of oxazole-4-carboxamides and their subsequent thermal rearrangement to 5-aminooxazole-4-carboxylates is optimized in a high-speed microwave-assisted procedure. The reaction sequence is effective with a variety of substituted oxazoles, and produces products in good yield and high purity.
Reaction of Acylaminobromomalonates and Acylaminobromoacetates with Trialkylphosphites - A Simple Synthesis of Ethyl 2-Amino-2-(diethoxyphosphoryl)acetate
Kober, Reiner,Steglich, Wolfgang
, p. 599 - 609 (2007/10/02)
Depending on the reaction conditions acylaminobromomalonates 1 and trialkylphosphites yield either 5-alkoxyoxazoles 7, 2-malonates 8, or 2-acylamino-2-(dialkoxyphosphoryl)malonates 2.N-Acylglucin esters 9 can be converted in
Cycloadditions of Isocyanides to Azomethine Ylides. Synthesis and Properties of 1-Phthalimidoazetidines
Charrier, Josiane,Foucaud, Andre',Person, Herve',Loukakou, Emile
, p. 481 - 486 (2007/10/02)
Reactions of isocyanides with 1-phthalimidoaziridines 1,5, and 11 gave 1-phthalimidoazetidines by cycloaddition to the azomethine ylides that are in equilibrium with the aziridines. (tert-Butylimino)azetidines and (tert-octylimino)azetidines rearranged into open-chain azadienes.Reactions of hydrazine hydrate with 1-phthalimidoazetidines did not give the corresponding N-aminoazetidines, but rather their decomposition products, nitrogen and enamino esters.
