Effect of several ionic liquids on the synthesis of 1,3-diphenyl-3-(phenylamino)propan-1-one in supercritical carbondioxide

Abstract

We found that in a scCO(2)-ionic liquid hybrid reaction system, Mannich reaction of benzaldehyde, aniline and acetophenone can be remarkably accelerated and the yield of Mannich base 1,3-diphenyl-3-(phenylamino)propan-1-one was significantly high. This system would be available for the green reactions with good performance

An Efficient, Mild, Solvent-Free, One-Pot Three-Component Mannich Reaction Catalyzed by (C4H12N2)2[BiCl6]Cl·H2O

“…1 H NMR (500 MHz, CDCl 3 ): δ = 8.17 (d, J = 8.7 Hz, 2 H), 7.90 (d, J = 7.4 Hz, 2 H), 7.65-7.55 (m, 3 H), 7.45 (t, J = 7.8 Hz, 2 H), 7.11 (t, J = 7.9 Hz, 2 H), 6.71 (t, J = 7.3 Hz, 1 H), 6.53 (d, J = 7.9 Hz, 2 H), 5.11 (t, J = 6.2 Hz, 1 H), 4.85 (s, 1 H), 3 ,72.82;H,5.24;N,8.09. Found: C,72.69;H,5.15;N,8.14.…”

“…As such, significant research efforts have been devoted to investigate other catalysts for the Mannich reaction in the past few decades, such as Lewis acids, 5 bases, 6 Brønsted acids, 7 and other organic additives. 8 Bismuth is the only stable heavy metal element in nature that is less toxic and radioactive than the other heavy metals, and its compounds have been of great value as metal catalysts in organic synthesis since the discovery of their catalytic activity. 9 Recent research has also been carried out with success in our laboratory to elaborate the ring-opening reactions of epoxides with anilines, 10 phenols, and thiophenols in the presence of bis(piperazine-1,4-diium) hexachlorobismuthate(III) chloride monohydrate [(C 4 H 12 N 2 ) 2 -[BiCl 6 ]Cl•H 2 O].…”