10557-79-6Relevant 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.
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 (
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.
SYNTHESIS OF 5-AMINO-4-CHLORO-4,5-DIHYDROISOXAZOLES AND 4-CHLOROISOXAZOLES.
Barluenga, Jose,Tomas, Miguel,Lopez, Luis Angel,Jardon, Jesus,Gotor, Vicente
, p. 1763 - 1774 (2007/10/02)
4-Chloro-4,5-dihydroisoxazoles (4) and (5) and -isoxazoles (6) were prepared by reaction of chlorodiimines (1) and (2) with hydroxylamine hydrochloride.Basic treatment of (5) gave rise to N-N bond formation yielding pyrazoles (8).
