110841-33-3Relevant academic research and scientific papers
Cationic gold(I)-catalyzed intramolecular cyclization of γ-hydroxyalkynones into 3(2H)-furanones
Egi, Masahiro,Azechi, Kenji,Saneto, Moriaki,Shimizu, Kaori,Akai, Shuji
supporting information; experimental part, p. 2123 - 2126 (2010/06/12)
"Chemical Equation Presented" The combination of (p-CF 3C6H4)3PAuCl and AgOTf generates a powerful catalyst for the intramolecular cyclizations of readily available y-hydroxyalkynones un-der mild conditions. The
Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)- furanones
Felman,Jirkovsky,Memoli,Borella,Wells,Russell,Ward
, p. 1183 - 1190 (2007/10/02)
In order to investigate new antiulcer agents, spizofurone 1 (AG-629) was fragmented and reassembled to generate 5-phenyl-2,2-dimethyl-3(2H)-furanone (bullatenone, 2). Because of the antiulcer activity of 2,5-phenyl-substituted 2,2-dimethyl-3(2H)-furanones (3-6) were made and shown to have poor activity. Insertion of an ethenyl link between the furanone and phenyl rings gave 5-(2- phenylethenyl)-2,2-dimethyl-3(2H)-furanone (7). This compound had better activity than 2. Compounds 8-41 were synthesized to evaluate the SAR in 5-(2- ethenyl substituted)-3(2H)-furanones. Electron-withdrawing substituents on the aromatic ring (8, 10, 19, and 20) gave 2-3-fold higher activity. Further increases in the activity were found when the phenyl ring was replaced by heterocyclic nuclei. Compounds that contained a thiophene (29), pyridine (24- 26), or quinoline ring (32) had the best activity. Replacement of the methyl group on the furanone ring with a phenyl (34) or p-fluorophenyl (40) substituent in the 2-pyridine series gave compounds with activity that ranked with the best obtained in this study. The best compounds from the above SAR studies were evaluated in the ethanol-necrosis model for duration of cytoprotection action. Compounds 19, 24, and 29, which had the best duration of action, were tested with AG-629 in the acidified aspirin and indomethacin- induced lesion models. Only compound 24 had equivalent activity with AG-629 in both models.
A NEW AND FACILE SYNTHESIS OF 3(2H)-FURANONES VIA CARBOXYLATION-DECARBOXYLATION SEQUENCE
Inoue, Yoshio,Ohuchi, Kunihiro,Imaizumi, Shin
, p. 5941 - 5942 (2007/10/02)
One-pot synthesis of 3(2H)-furanones from α-ethynyl tertiary alcohols and acyl halides has been achieved in the presence of a palladium complex under CO2 pressure.
