Alkylation of pyridine 1-oxides and related compounds with activated acetylenes. A novel molecular rearrangement of heteroaromatic N-oxides was written by Abramovitch, Rudolph A.;Grins, George;Rogers, Richard B.;Shinkai, Ichiro. And the article was included in Journal of the American Chemical Society in 1976.Computed Properties of C7H9NO This article mentions the following:
The reaction of pyridine 1-oxide with phenylcyanoacetylene gives the 3-alkylated derivative (I) as the main product together with minor amounts of II, III and IV. With substituted pyridine 1-oxides and with quinoline 1-oxide the products of 3-alkylation are also formed unless the 3 and 5 positions are blocked. The 3-alkylated products arise from the initial 1,2-dihydro adduct by a [σ2s + π2a + π4s] rearrangement, followed by regiosp. cyclopropane ring opening to the 3-alkylated derivatives In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Computed Properties of C7H9NO).
3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Computed Properties of C7H9NO