Reaction of aromatic N-oxides with dipolarophiles. XI. 1,3-Dipolar cycloaddition reaction of pyridine N-oxides with tosyl isocyanate and one-pot synthesis of 2-oxooxazolo[4,5-b]pyridine derivatives was written by Hisano, Takuzo;Harano, Kazunobu;Fukuoka, Ryuichi;Matsuoka, Toshikazu;Muraoka, Keiji;Shinohara, Ikuo. And the article was included in Chemical & Pharmaceutical Bulletin in 1986.Application In Synthesis of 3,5-Dimethylpyridine 1-oxide This article mentions the following:
The cycloaddition reactivity of 4-MeC6H2SO2NCO toward pyridine N-oxides was calculated by the CNDO/2 method using a perturbation equation, and the results indicated that the initial stage of the reaction might be controlled by coulombic attraction. The 1,3-dipolar cycloaddition reaction of 4-MeC6H4SO2NCO with 2 equivalent of 3,5-dibromopyridine N-oxide in refluxing C6H6 gave 6-bromo-2-oxooxazolo[4,5-b]pyridine, whereas the use of 1 equivalent of 3,5-dichloropyridine N-oxide gave 6,7a-dichloro-2-oxo-3-tosyl-3a,7a-dihydrooxazolo[4,5-b]pyridine, formed from the 1,5-sigmatropic rearrangement of the primary cycloadduct. When the reaction was carried out in the presence of Et3N in C6H6 6-halo-2-oxo-3-tosyloxazolo[4,5-d]pyridine was isolated. The observed activation parameters, as well as the small solvent effects, may be interpreted in terms of a concerted pathway. The reaction should be very valuable as a one-pot synthesis of 2-oxooxazolo[4,5-b]pyridines, which are pyridine analogs of 5-chloro-2-benzoxazolinone. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Application In Synthesis of 3,5-Dimethylpyridine 1-oxide).
3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Application In Synthesis of 3,5-Dimethylpyridine 1-oxide