Ultrasound-assisted rapid synthesis of β-aminoketones with direct-type catalytic Mannich reaction using bismuth(III) triflate in aqueous media at room temperature

Abstract

An innovative, powerful, efficient and relatively rapid method was developed to synthesise various β-aminoketone derivatives from cyclohexanone, substituted aromatic amines and aromatic or hetero-aromatic aldehydes via ultrasound-assisted direct-type catalytic Mannich reaction using bismuth(III) triflate in water. Good yields of the desired β-aminoketones were obtained at room temperature by ultrasound-assisted reaction within 1–2 h. The major advantages of the proposed method are undemanding conditions, easy operation, low toxicity, shorter reaction time, anti selectivity and higher yields in comparison with conventional methods.

Ultrasonic synthesis, characterization of β-aminoketones by bismuth(III) triflate and determination of antigenotoxic properties

“…The solvents were removed under reduced pressure. The crude mixture was purified either by column chromatography (hexane/etoac) or by recrystallization in hexane, giving the diastereoisomeric mixture of β-aminoketone (Ozturkcan et al, 2012a) (Table 1 4a-e).…”

“…The results were summarized in Table 1. After the purification processes, the structures of the obtained new compounds have been clarified by spectroscopic methods (Fourier-transform infrared [FT-IR], proton nuclear magnetic resonance [ 1 H-NMR], carbon 13 nuclear magnetic resonance [ 13 C-NMR], elemental analysis [EA] and mass spectrometry [MS]) (Ozturkcan et al, 2012a). All compounds were summarized in Figure 2.…”

“…In addition, the study was designed to evaluate the antimutagenic potential of five b-aminoketones compounds using Ames/Salmonella and Escherichia coli WP2 bacterial reverse mutation assay systems. To the best of our knowledge, only one report on determination of mutagenic/antimutagenic activities was published by our research group for two of these compounds with different bacteria system, and there is no report on three of them with any bacteria system (Ozturkcan et al, 2012a(Ozturkcan et al, , 2012b.…”

Using free radical polymerization and Mannich reaction, synthesis and characterization of cationic polyacrylamides having similar molecular weight but different charge densities

“…Mannich reaction was utilized for varied organic synthesis apart from polyelectrolyte synthesis, one such application used for β-aminoketones synthesis from cyclohexanone compounds to assess the mutagenic and antimutagenic potential of synthesized β-aminoketones using bacteria [11,12]. The synthetic β-aminoketones, which is a Mannich base derivative produced in the reaction of an amine, an aldehyde (formaldehyde), and a carbon acid, have a great potential to be industrial candidates for medicinal applications [13].…”

Screening Approach for Chiral Separation of β‐Aminoketones by HPLC on Various Polysaccharide‐Based Chiral Stationary Phases

“…The Mannich reaction is one of the most-studied MCRs, discovered in 1912; 1-3 the product is an imino analog of the aldol condensation. 4 It is one of the most important carboncarbon bond formation reactions in organic synthesis, [5][6][7][8][9][10][11][12][13][14] in which an aminomethyl group is introduced to the α position of a carbonyl function. 3,15 In the classical condensation, a single carbon atom is attached to an active methylene or methine group, using formaldehyde and an amine, to generate β-amino carbonyl compounds (Mannich bases), which are highly useful chiral building blocks 16,17 and important intermediates for the synthesis of various pharmaceutical and natural product synthesis including β-amino alcohols, β-amino acids, and β-lactams.…”