Carbon-based Solid Acid Catalyzed One-pot Mannich Reaction: A Facile Synthesis of β-Amino Carbonyl Compounds

Abstract

A simple and efficient method for the synthesis of β-amino carbonyl compounds by one-pot three-component Mannich reaction of acetophenone, aromatic aldehydes and aromatic amines using a carbon-based solid acid (CBSA), as an effective and reusable catalyst, is described. The present methodology offers several advantages such as simple procedure with an easy work-up, shorter reaction times, and high yields.

Polymer Support Immobilized Acidic Ionic Liquid: Preparation and Its Application as Catalyst in the Synthesis of Hantzsch 1,4-Dihydropyridines

“…The weightaverage molecular weight (M w ) and number-average molecular weight (M n ) were determined by GPC analysis (Figure 2 4 ] in EtOH at reflux temperature (entry 4). Greater amounts of the catalyst were found to have an inhibitory effect on the formation of the product (entries 5,6).…”

“…[1][2][3][4][5] The major problem associated with most homogenous catalyst systems is the separation of catalyst from the reaction mixture and the recycling of the catalyst. Heterogeneous catalysts can be easily separated from the reaction products and reused in successive runs.…”

“…According to this method and due to our interest in the applications of reusable catalysts in organic reactions [40][41][42][43][44][45][46][47] …”

An Eco-Friendly Protocol for Synthesis of β- aminoketones via Mannich Reaction Using Citric Acid: A Biodegradable Catalyst

“…β-amino carbonyl derivatives are found in a number of biologically active natural products [5]. The reported Mannich reactions have been catalyzed by various Lewis or Brønsted acid catalysts such as silica-supported AlCl 3 [6], CeCl 3 .7H 2 0 [7], NbCl 5 [8], BiCl 3 [9], CAN [10], HClO 4 -SiO 2 [11], Bi(OTf) 3 [12], Zn(OTf) 2 [13], ionic liquid [14][15][16][17], sulphamic acid [18][19][20], Fe(Cp) 2 PF 6 [21], Cu-nanoparticles [22], [RE(PFO) 3 ] [23], silica based tin(II) catalyst [24], PEG-SO 3 H [25] ZSM-5-SO 3 H [26], carbon based solid acid [27], polyaniline/SiO 2 [28], lipase [29], saccharose [30], heteroplyacid salts [31]. However, most of the reported methods for the Mannich reaction suffer from drawbacks such as long reaction times and harsh reaction conditions, toxicity, and difficulty in product separation, which limit its use in the synthesis of complex molecules.…”

Carbon-Based Solid Acid Catalyzed Synthesis of Polyhydroquinoline Derivatives via Hantzsch Reaction Under Solvent-Free Conditions

“…Therefore, due to the increasing demand in modern organic processes for avoiding expensive purification, and in continuation of our previous works on the applications of reusable catalysts in the synthesis of organic compounds [28][29][30][31][32][33][34][35][36] , we report herein a new and efficient synthesis of polyhydroquinoline derivatives using a one-pot, four-component Hantszch condensation of dimedone, aryl aldehydes, ethyl acetoacetate and ammonium acetate using a catalytic amount of CBSA under solvent-free conditions (Scheme 1). Scheme 1.…”