650600-09-2Relevant academic research and scientific papers
Complementary regioselective synthesis of 3,5-disubstituted isoxazoles from ynones
Liu, Xiaochen,Hong, Dongsub,She, Zhigang,Hersh, William H.,Yoo, Barney,Chen, Yu
, p. 6593 - 6606 (2018/10/05)
Two regioselective synthetic routes towards 3,5-disubstituted isoxazoles from ynones are reported. One route takes place via first converting the ynones to ynone O-methyl oximes, followed by a palladium-catalyzed intramolecular cyclization. The other invo
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 (
Stereospecific Suzuki, Sonogashira, and Negishi coupling reactions of N-alkoxyimidoyl iodides and bromides
Dolliver, Debra D.,Bhattarai, Bijay T.,Pandey, Arjun,Lanier, Megan L.,Bordelon, Amber S.,Adhikari, Sarju,Dinser, Jordan A.,Flowers, Patrick F.,Wills, Veronica S.,Schneider, Caroline L.,Shaughnessy, Kevin H.,Moore, Jane N.,Raders, Steven M.,Snowden, Timothy S.,McKim, Artie S.,Fronczek, Frank R.
, p. 3676 - 3687 (2013/06/04)
A high-yielding stereospecific route to the synthesis of single geometric isomers of diaryl oxime ethers through Suzuki coupling of N-alkoxyimidoyl iodides is described. This reaction occurs with complete retention of the imidoyl halide geometry to give single E- or Z-isomers of diaryl oxime ethers. The Sonogashira coupling of N-alkoxyimidoyl iodides and bromides with a wide variety of terminal alkynes to afford single geometric isomers of aryl alkynyl oxime ethers has also been developed. Several of these reactions proceed through copper-free conditions. The Negishi coupling of N-alkoxyimidoyl halides is introduced. The E and Z configurations of nine Suzuki-coupling products and two Sonogashira-coupling products were confirmed by X-ray crystallography.
Synthesis of trisubstituted isoxazoles by palladium(ii)-catalyzed cascade cyclization-alkenylation of 2-alkyn-1-one o -methyl oximes
She, Zhigang,Niu, Dongyue,Chen, Lei,Gunawan, Maria A.,Shanja, Xhesika,Hersh, William H.,Chen, Yu
, p. 3627 - 3633 (2012/06/15)
A palladium-catalyzed, cascade 5-endo-dig cyclization-alkenylation synthesis of isoxazoles has been developed. The addition of 1 equiv of n-Bu 4NBr significantly increases the yield of the desired 4-alkenyl-3,4,5-trisubstituted isoxazoles. A va
