102233-68-1Relevant articles and documents
Iminium Ion Mediated Cyclizations of 4-Aryl-1,4-dihydropyridines. Bridging from Nitrogen with Thiophene and an Olefin
Hartman, George D.,Halczenko, Wasyl,Phillips, Brian T.,Pitzenberger, Steven M.
, p. 2202 - 2205 (2007/10/02)
Novel 4-aryl-1,4-dihydropyridines, possessing 2-(3-thienyl)ethyl and 1-buten-4-yl nitrogen substitution, have been prepared by a titanium-promoted Hantzsch-type condensation.Treatment of these dihydropyridines with titanium tetrachloride catalyzes generation of the dihydropyridine/iminium ion.Subsequent trapping of this ion by either the thienyl or the olefinic moiety affords cyclic products derived respectively from elimination or addition pathways available to the intermediate cation.The stereochemistry of these cyclizations is discussed, and the scope of the process is evaluated in light of N-substituted dihydropyridines that do not cyclize