39588-76-6Relevant academic research and scientific papers
Friedel-Crafts tetraacylation of isobutene precursors: scope and limitations of a new and general synthesis of 1,3,6,8-tetraalkyl-2,7-naphthyridines
Erre, Claude H.,Rousell, Christian
, p. 449 - 453 (2007/10/02)
Isobutene generated in situ from various precursors (t-BuOH, t-BuCl, diisobutylene and isooctane) is diacylated and tetraacylated by RCOCl (R = methyl, ethyl, propyl, butyl and iso-propyl) in the presence of a Lewis acid (AlCl3, AlBr3, FeCl3, TiCl3, TiCl4, SnCl4, ZnCl2).The reaction can be performed with or without solvent.Already reported compounds such as 4-acetonylidene-2,6-dimethyl-(4H)-pyrane 2 and 4-acetonyl-2,6-dimethylpyridine 3 arise from acetyl cleavage of the tetraacylated compound and are not produced by direct triacetylation of isobutene.The tetraacylation products are easily transformed into the previously inaccessible 1,3,6,8-tetraalkyl-2,7-naphthyridines 4a-d when liquid ammonia is used for the post reaction treatment.
