22020-72-0Relevant articles and documents
A One Step Transformation of the Sodium Salt of α-aci-Nitrotoluene into 3,4,5-Triphenylisoxazole
Fukunaga, Kimitoshi,Okamoto, Akihiko,Furumoto, Keiji,Kimura, Makoto
, p. 3045 - 3046 (1982)
3,4,5-Triphenylisoxazole was produced by the reaction of the sodium salt of α-aci-nitrotoluene with the 1-cyano-1-methylethyl radical.The reaction was found to proceed via one electron transfer from α-aci-nitrotoluene anion to a 1-cyano-1-methylethyl radi
Synthesis of 3,5-Disubstituted Isoxazoles through a 1,3-Dipolar Cycloaddition Reaction between Alkynes and Nitrile Oxides Generated from O-Silylated Hydroxamic Acids
Carloni, Laure-Elie,Mohnani, Stefan,Bonifazi, Davide
, p. 7322 - 7334 (2019/11/05)
In this paper, we report the regioselective synthesis of 3,5-disubstituted isoxazoles by 1,3-dipolar cycloaddition between alkynyl dipolarophiles and nitrile oxide dipoles generated in-situ from O-silylated hydroxamic acids in the presence of trifluoromethanesulfonic anhydride and NEt3. Thanks to the mild, metal-free and oxidant-free conditions that this strategy offers, the reaction was successfully applied to a wide variety of alkynyl dipolarophiles, demonstrating the tolerance of this approach to diverse functional groups. In particular, we have shown that the method was compatible with biological molecules such as peptides and peptide nucleic acids (PNA). This protocol constitutes another example of metal-free 1,3-dipolar cycloaddition leading to the regioselective formation of isoxazoles.
TEMPO-mediated aliphatic C-H Oxidation with Oximes and hydrazones
Zhu, Xu,Wang, Yi-Feng,Ren, Wei,Zhang, Feng-Lian,Chiba, Shunsuke
supporting information, p. 3214 - 3217 (2013/07/26)
A method for aliphatic C-H bond oxidation of oximes and hydrazones mediated by 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) has been developed, which enables the concise assembly of substituted isoxazole and pyrazole skeletons.