One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions

Abstract

An environmentally-friendly, one-pot multicomponent reaction of various aldehydes, amines and nitroalkanes for the synthesis of β-nitroamines is here described. Amberlyst A-21 supported CuI was found to be a highly efficient novel heterogeneous catalyst for the three-component nitro-Mannich reaction between aldehydes, amines and nitroalkanes. The developed protocol is performed in a solvent-free medium to produce a variety of β-nitroamines in good to excellent yields within short reaction times. The catalyst can be easily prepared and recovered. It has been tested up to eight times with only a minor activity loss.

Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones

“…It should be mention that the formation of 1,4-addition product 15 was not observed ( Table 1 , entry 3). An application of basic amberylst [ 54 ] resulted in the formation of target product 1 with a reduced reaction yield (18%, Table 1 , entry 4), while the application of quaternary ammonium based Dowex-1 provided p -quinol 1 with 68% ( Table 1 , entry 5). Ionic polymers like Dowex-1 were already found to be efficient support for CuI catalysts in Huisgen’s 1,3-dipolar cycloaddition [ 55 ].…”

Facile Multicomponent Mannich Reaction towards Biologically Active Compounds

“…The application of CuI supported on Amberlyst A21 was documented for such a reaction, without the need of other solvents with yields ranging between 38-98 % (Scheme 8). [46] Scheme 3. Wang et.…”

Recent Advances in Multicomponent Reactions Catalysed under Operationally Heterogeneous Conditions

“…Lastly, tertiary amines performed poorly, and heating was needed (33-47%,18-24 h) [94]. Another member of the Mannich-type reaction is the aza-Henry, or nitro-Mannich reaction, which involves the combination of aldehydes, amines, and nitroalkanes (Figure 40) [95]. The use of copper(I) iodide supported on Amberlyst A21 was reported for such a reaction, and did not require the addition of other solvents (even if nitromethane was used in large excess to act as a reactant and solvent simultaneously).…”

“…The use of copper(I) iodide supported on Amberlyst A21 was reported for such a reaction, and did not require the addition of other solvents (even if nitromethane was used in large excess to act as a reactant and solvent simultaneously). Reaction times varied be- Another member of the Mannich-type reaction is the aza-Henry, or nitro-Mannich reaction, which involves the combination of aldehydes, amines, and nitroalkanes (Figure 40) [95]. The use of copper(I) iodide supported on Amberlyst A21 was reported for such a reaction, and did not require the addition of other solvents (even if nitromethane was used in large excess to act as a reactant and solvent simultaneously).…”