83300-85-0Relevant articles and documents
1,4-Dihydropyridine/BF3OEt2 for the reduction of imines: Influences of the amount of added BF3OEt2 and the substitution at N-1 and C-4 of the dihydropyridine ring
Zattoni, Ingrid F.,Guanaes, Lais D.,Cerqueira, Letícia B.,Pontarolo, Roberto,Ducatti, Diogo R.B.,Duarte, M. Eugênia R.,Noseda, Miguel D.,Trindade, Angela C.L.B.,Gon?alves, Alan G.
supporting information, (2019/09/12)
We have evaluated four 1,4-dihydropyridines (DHPs 1a, 1b, 1c and 1d) as reducing agents, which presented free (hydrogenated) or phenyl-substituted N-1 and C-4 positions of the DHP ring. Reactions combining each of the DHP and different amounts of BF3OEt2 were evaluated for the reduction of imine 2a (N-benzylideneaniline). DHP simultaneously substituted at N-1 and C-4 (1a), and DHP substituted at C-4 (1b) gave lower yields for reduction of 2a in comparison with DHPs 1c and 1d (both unsubstituted at the C-4 position). By evaluating the amount of added BF3OEt2 to the reaction mixture, we have found that DHP 1c (substituted at N-1) provided its best yield for amine 3a (82%) when associated with stoichiometric amounts BF3OEt2, while DHP 1d (N-1- and C-4-unsubstituted derivative) was more effective (90% yield) with catalytic quantities of the Lewis acid. The reaction system using DHP 1c under stoichiometric BF3OEt2 could also be successfully applied with additional imine examples and under reductive amination conditions.
