30740-94-4Relevant academic research and scientific papers
Vinyl Azides in Heterocyclic Synthesis. Part 10. Synthesis of the Isoindolobenzazepine Alkaloid Lennoxamine
Moody, Christopher J.,Warrellow, Graham J.
, p. 2929 - 2936 (2007/10/02)
A total synthesis of the isoindolobenzazepine alkaloid lennoxamine (1), by a route involving vinyl azide chemistry, is described.Model studies on the azidocinnamates (12) and (13) revealed a striking difference between the (E)- and (Z)-isomers; whereas the (Z)-isomer (12) gave largely the 1-benzylisoquinoline (15) on decomposition, the (E)-isomer (13) gave the 2-aryl-3-benzazepine (14) as the major product.Consequently, in the lennoxamine synthesis, the azidocinnamate (26) bearing the (E)-alkenyl side chain, prepared from 6-bromopiperonal via the (E)-stilbene aldehyde (25) (Scheme 4), was decomposed to give the key 2-aryl-3-benzazepin e (27).Reduction of the double bonds in (27) was accompanied by cyclisation to the tetrahydroisoindolobenzazepine (30), which was converted into lennoxamine (1) by reduction of the ester group to an aldehyde, and decarbonylation.
