Categories: N-O Bond Formation >
Synthesis of N-oxides of pyridines and related compounds
Recent Literature
Sodium percarbonate is an ideal and efficient oxygen source for the oxidation of
tertiary nitrogen compounds to N-oxides in excellent yields in the
presence of various rhenium-based catalysts under mild reaction conditions.
S. L. Jain, J. K. Joseph, B. Sain, Synlett, 2006,
2661-2663.
The use of titanium silicalite (TS-1) in a packed-bed microreactor and H2O2
in methanol as solvent enable the formation of various pyridine N-oxides
in very good yields. This flow process is a safer, greener, and more highly
efficiency process than using a batch reactor. The device was used for over 800
hours of continuous operation while while the catalyst remained active.
S. Chen, S. Yang, H. Wang, Y. Niu, Z. Zhang, B. Qian, Synthesis, 2022, 54,
3999-4004.
Sodium perborate in acetic acid is an effective reagent for the oxidation of
aromatic aldehydes to carboxylic acids, iodoarenes to (diacetoxyiodo)arenes,
azines to N-oxides, and various sulphur heterocycles to S,S-dioxides.
Nitriles undergo smooth oxidative hydration to amides when aqueous methanol
is employed as solvent.
A. McKillop, D. Kemp, Tetrahedron, 1989,
45, 3299-3306.
Urea-hydrogen peroxide adduct (UHP) is stable, inexpensive and an easily handled
reagent. UHP is used in an efficient solid state oxidation of different
organic molecules: hydroxylated aldehydes and ketones (to hydroxylated phenols),
sulfides (to sulfoxides and sulfones), nitriles (to amides) and nitrogen
heterocycles (to N-oxides).
R. S. Varma, K. P. Naicker, Org. Lett., 1999, 1,
189-191.
Use of a solvent with greater density than the fluorous phase is an
alternative to the U-tube method in phase-vanishing reactions in cases where
both reactants are less dense than the fluorous phase.
N. K. Jana, J. G. Verkade, Org. Lett., 2003, 5,
3787-3790.