Reaction of aromatic N-oxides with dipolarophiles. XII. Stereoselective exo cycloaddition of 3,5-lutidine N-oxide with N-substituted maleimides and a frontier molecular orbital and mechanistic study was written by Hisano, Takuzo;Harano, Kazunobu;Matsuoka, Toshikazu;Yamada, Hirotoshi;Kurihara, Masahiko. And the article was included in Chemical & Pharmaceutical Bulletin in 1987.Reference of 3718-65-8 This article mentions the following:
Pericyclic reactions of 3,5-lutidine N-oxide with N-phenylmaleimides were investigated. The primary cycloadducts are thermally labile and undergo 1,5-sigmatropic rearrangement to give the 2,3-dihydropyridine derivatives The proton NMR structural assignment of the 1,5-sigmatropy products implies that the primary cycloaddition proceeds through an exo transition state. The reaction behavior is discussed in terms of frontier MO theory, based on MINDO/3 and CNDO/2 calculations and kinetic data. The reaction falls into the category of a normal-type cycloaddition and the exo cycloaddition is brought about by the unfavorable secondary orbital interaction. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Reference of 3718-65-8).
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. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Reference of 3718-65-8