Reaction of pyridine 1-oxides with benzyne. β-Hydroxyarylation of pyridines via {σ2s + π2a + π4s rearrangements was written by Abramovitch, Rudolph A.;Shinkai, Ichiro. And the article was included in Journal of the American Chemical Society in 1974.Synthetic Route of C7H9NO This article mentions the following:
Pyridine 1-oxides react with benzyne to give mainly the corresponding 3-(ο-hydroxyphenyl)-pyridines via a novel [σ2s + π2a + π4s] rearrangement. If the pyridine β-positions are blocked 3,5-disubstituted 2-(ο-hydroxyphenyl) pyridines are formed. Unusual dihydropyridine intermediates leading to the latter compounds were isolated and characterized. Addnl. evidence for a 2,3-dihydropyridine intermediate I (R = R1 = Me) was adduced from the reaction of 3,5-dichloropyridine 1-oxide with benzyne which led to 3-chloropyrido[3,2-b]benzofurn I (R = H, R1 = Me) in good yield. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Synthetic Route of C7H9NO).
3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C7H9NO