24372-51-8Relevant academic research and scientific papers
Investigation of the [1,5]-hydride shift as a route to nitro-Mannich cyclisations
Anderson, James C.,Chang, Chia-Hao,Corpinot, Mérina K.,Nunn, Michael,Ware, Oliver J.
, (2019)
Conditions were found for the [1,5]-hydride shift nitro-Mannich reaction that led to the synthesis of 2,3-disubstituted tetrahydroquinolines. Two simple cyclic amine substrates gave diastereomerically pure rearranged products in 65 and 90% yields by refluxing in HFIP. A more general procedure used Gd(OTf)3 as a catalyst and successfully rearranged other cyclic and acyclic amines in 42–84% yield with diastereomeric ratios of 75:25 to >95:5 in favour of the anti-diastereoisomer (9 examples). Two examples of sulphur containing heterocycles gave lower yields of 9 and 25%. Electron withdrawing substituents were shown to have a deleterious effect on the success of the reaction. The results indicated the limitation of the [1,5]-hydride shift nitro-Mannich reaction with respect to the stability of the intermediate iminium ion.
Convenient amination of weakly activated thiophenes, furans and selenophenes in aqueous media
Prim, Damien,Kirsch, Gilbert
, p. 6511 - 6526 (2007/10/03)
We describe herein a new amination procedure of weakly activated heterocyclic bromo derivatives in aqueous media. The base catalysed mechanism of this reaction is also confirmed. Moreover, the application of this strategy to the preparation of amino furans and selenophenes is outlined.
