33318-76-2Relevant academic research and scientific papers
Chemodivergent Synthesis of Oxazoles and Oxime Ethers Initiated by Selective C-N/C-O Formation of Oximes and Diazo Esters
Qi, Zhenjie,Wang, Shaozhong
supporting information, p. 8549 - 8553 (2021/10/25)
Chemodivergent reactions of oximes and diazo esters involving Rh-catalyzed [3+2] annulation and photodriven O-H insertion have been developed to generate oxazoles and oxime ethers. A range of aldehyde and ketone oximes reacted with α-diazocarbonyl compounds in a controllable manner in which functional groups, including ketone, ester, amide, ether, thiol ether, silane, alkene, allene, and alkyne groups, were well tolerated.
Synthesis and preliminary anti-inflammatory and anti-bacterial evaluation of some diflunisal aza-analogs
Carta, Davide,Brun, Paola,Dal Pra, Matteo,Bernabè, Giulia,Castagliuolo, Ignazio,Ferlin, Maria Grazia
, p. 1017 - 1032 (2018/06/27)
Our aim was to identify new multi-target compounds endowed with both anti-inflammatory and anti-bacterial activities for treatment of human infections. Diflunisal, a nonsteroidal anti-inflammatory agent, has recently been repurposed for its anti-virulence properties against methicillin-resistant Staphylococcus aureus. Effective synthesis of some aza-analogs of the anti-inflammatory drug diflunisal was carried out following the route involving key oxazole intermediates to obtain o- and m-hydroxypyridinecarboxylic acid derivatives. The newly synthesized diflunisal aza-analogs did not exhibit cytotoxic activity up to 80 μM and some of them exhibited anti-inflammatory activities, decreasing the levels of pro-inflammatory cytokines and prostaglandins induced by bacterial lipopolysaccharide in human primary macrophages. Ten of the diflunisal aza-analogs were found to have interesting antibacterial activity, sensitizing S. aureus, Streptococcus pyogenes, Enterococcus faecium, and Pseudomonas aeruginosa to the antibacterial effects of beta-lactam antibiotics and protein synthesis inhibitors.
Metal-free decarboxylative Hetero-Diels-Alder synthesis of 3-hydroxypyridines: A rapid access to N-fused bicyclic hydroxypiperidine scaffolds
Jouanno, Laurie-Anne,Di Mascio, Vincent,Tognetti, Vincent,Joubert, Laurent,Sabot, Cyrille,Renard, Pierre-Yves
, p. 1303 - 1319 (2014/03/21)
A complete experimental and theoretical study of the thermally controlled metal-free decarboxylative hetero-Diels-Alder (HDA) reaction of 5-alkoxyoxazoles with acrylic acid is reported. This strategy offers a new entry to valuable 2,6-difunctionalized 3-hydroxypyridines from readily available 2- and 4-disubstituted 5-alkoxyoxazoles. The reaction conditions proved compatible with, among others, ketone, amide, ester, ether, and nitrile groups. The broad functional group tolerance of the protocol allows a rapid and versatile access to both hydroxyindolizidine and hydroxyquinolizidine derivatives via a pyridine dearomatization strategy.
Expeditious microwave-assisted synthesis of 5-alkoxyoxazoles from α-triflyloxy esters and nitriles
Jouanno, Laurie-Anne,Sabot, Cyrille,Renard, Pierre-Yves
, p. 8549 - 8555 (2012/11/07)
A rapid and general access to diversely substituted 5-alkoxyoxazoles 2 (i.e., R1, R2 = alkyl, phenyl) from easily accessible α-triflyloxy/hydroxy esters 1 and nitriles with good yields (41-76%) is reported. The versatility of the cyc
New efficient synthesis of 5-ethoxyoxazoles and oxazolo[3,2-c]quinazolines via aza-Wittig reaction
Huang, Nian-Yu,Nie, Yi-Bo,Ding, Ming-Wu
experimental part, p. 611 - 614 (2009/06/28)
5-Ethoxyoxazoles or 2-acylamino propanoates were synthesized by aza-Wittig reaction of iminophosphorane with acyl chloride in the presence of triethylamine. Reactions of 5-alkoxyoxazole with triphenyphosphine produced iminophosphoranes. A tandem aza-Wittig reaction of iminophosphorane with isocyanate or carbon disulfide generated oxazolo[3,2-c]quinazolines in satisfactory yields. Georg Thieme Verlag Stuttgart.
