650600-16-1Relevant academic research and scientific papers
Isomerizable (: E / Z)-alkynyl- O -methyl oximes employing TMSCl-NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles
Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
, p. 48666 - 48675 (2016/06/09)
For the first time, 4-chloroisoxazoles are directly synthesized in moderate to excellent yields from (E/Z)-alkynyl-O-methyl oximes via chlorinative cyclization. The synthesis employs the combination of N-chlorosuccinimide (NCS) and chlorotrimethylsilane (
Synthesis of 3,4,5-trisubstituted isoxazoles through gold-catalyzed cascade cyclization-oxidative alkynylation and cyclization-fluorination of 2-alkynone O-methyloximes
Song, Doo-Hee,Ryu, Jae-Sang
, p. 2635 - 2644 (2015/04/22)
Gold-catalyzed tandem cyclization-oxidative alkynylation and cyclization-fluorination reactions of 2-alkynone O-methyloximes are described. The reactions proceed smoothly at room temperature in the presence of 10 mol % of (PPh3)AuNTf2, 2.5 equivalents of selectfluor, and 2 equivalents of K3PO4. 2-Alkynone O-methyloximes undergo intramolecular oxyauration/cyclization and ensuing oxidative cross-coupling and fluorination process to afford the corresponding 3,4,5-trisubstituted isoxazoles in a cascade manner.
Direct synthesis of 4-fluoroisoxazoles through gold-catalyzed cascade cyclization-fluorination of 2-alkynone O-methyl oximes
Jeong, Yunkyung,Kim, Bom-I,Lee, Jae Kyun,Ryu, Jae-Sang
, p. 6444 - 6455 (2014/08/05)
A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol
The synthesis of highly substituted isoxazoles by electrophilic cyclization: An efficient synthesis of valdecoxib
Waldo, Jesse P.,Larock, Richard C.
, p. 9643 - 9647 (2008/03/17)
(Chemical Equation Presented) A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.
