24768-82-9Relevant academic research and scientific papers
R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond
Bondarenko, Oksana B.,Karetnikov, Georgy L.,Komarov, Arseniy I.,Pavlov, Aleksandr I.,Nikolaeva, Svetlana N.
supporting information, p. 322 - 332 (2021/01/14)
A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.
Synthesis of C4-alkynylisoxazoles: Via a Pd-catalyzed Sonogashira cross-coupling reaction
Yang, Wen,Yao, Yongqi,Yang, Xin,Deng, Yingying,Lin, Qifu,Yang, Dingqiao
, p. 8894 - 8904 (2019/03/28)
A Pd-catalyzed Sonogashira cross-coupling reaction for the synthesis of C4-alkynylisoxazoles from 3,5-disubsitituted-4-iodoisoxazoles and terminal alkynes was described, which could afford the corresponding products with high yield (up to 98%). The result
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 (
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.
Synthesis of isoxazoles via electrophilic cyclization
Waldo, Jesse P.,Larock, Richard C.
, p. 5203 - 5205 (2007/10/03)
(Chemical Equation Presented) A variety of 3,5-disubstituted 4-halo(seleno)isoxazoles are readily prepared in good to excellent yields under mild reaction conditions by the reaction of 2-alkyn-1-one O-methyl oximes with ICI, I2, Br2,
Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides
Day, Ruth Ann,Blake, Jacqueline A.,Stephens, Chad E.
, p. 1586 - 1590 (2007/10/03)
The convenient C-4 halogenation of 3,5-diarylisoxazoles using N-halosuccinimides (NBS, NCS, or NIS) in acetic acid is described. A strong acid catalyst was required for efficient halogenation of some isoxazoles depending on the substituent on the 5-phenyl ring. Finally, the 4-iodoisoxazoles were found to undergo a novel proto-deiodination upon heating in the presence of H2SO4.
