Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles >
Synthesis of 1,2,4-oxadiazoles
Recent Literature
PTSA-ZnCl2 is an efficient and mild catalyst for the synthesis of
3,5-disubstituted-1,2,4-oxadiazoles from amidoximes and organic nitriles.
J. K. Augustine, V. Akabote, S. G. Hegde, P. Alagarsamy, J. Org. Chem., 2009,
74, 5640-5643.
A one-pot reaction between nitriles, hydroxylamine and Meldrum’s acids under
microwave irradiation and solvent-free conditions gives 3,5-disubstituted
1,2,4-oxadiazoles in good to excellent yields.
M. Adib, M. Mahdavi, N. Mahmoodi, H. Pirelahi, H. R. Bijanzadeh, Synlett, 2006,
1765-1767.
Iron(III) nitrate mediates a selective synthesis of 3-acyl-1,2,4-oxadiazoles
from alkynes and nitriles. A nitration of alkynes leads to α-nitroketones,
dehydration of α-nitroketones provides the nitrile oxides, and a subsequent 1,3-dipolar
cycloaddition of nitrile oxides with nitriles produces 3-acyl-1,2,4-oxadiazoles.
Q. Bian, C. Wu, J. Yuan, Z. Shi, T. Ding, Y. Huang, H. Xu, Y. Xu, J. Org. Chem., 2020, 85,
4058-4066.
Synthetically useful aminodioximes are prepared via a novel three-component
reaction of Z-chlorooximes, isocyanides, and hydroxylamines. Furthermore,
a Mitsunobu-Beckmann rearrangement of aminodioximes yields
1,2,3-oxadiazole-5-amines.
V. Mercalli, A. Massarotti, M. Varese, M. Giustiniano, F. Meneghetti, E.
Novellino, G. C. Tron, J. Org. Chem.,
2015,
80, 9652-9661.
2,2,2-trifluoroacetaldehyde O-(aryl)oxime releases CF3CN in
quantitative yield under mildly basic conditions. 2,2,2-trifluoroacetaldehyde
O-(aryl)oxime was successfully used in the synthesis of trifluoromethylated
oxadiazoles.
B. Lin, Y. Yao, Y. Huang, Z. Weng, Org. Lett.,
2022, 24, 2055-2058.
A series of α-amino acid-derived 1,2,4-oxadiazoles have been synthesized via a
convenient and inexpensive one-pot protocol in good yields and in relatively
short reaction times.
A. L. Braga, D. S. Lüdtke, E. E. Alberto, L. Dornelles, W. A. Severo Filho, V.
A. Corbellini, D. M. Rosa, R. S. Schwab, Synthesis, 2004,
1589-1594.