One-pot Three-component Mannich Reaction Research Articles

A Heterogeneous, Highly Efficient, and Reusable Mo-Al2O3 Composites Based Organocatalyst for One Pot Three-Component Mannich Reaction for the Synthesis of β-aminocarbonyl Compounds

We have successfully developed a new Mo-Al2O3/p-TSA organocatalyst which has improved the yield of the Mannich reaction. This protocol has the advantage of mild conditions, high yield, easy work-up, environmentally friendly procedure, and the solid catalyst was recycled. The catalyst was analysed by XRD, SEM, and EDS techniques. The synthesized Mo-Al2O3composites were used in the presence of p-toluene sulfonic acid (p-TSA) conducts the one-pot three-component Mannich reaction and various β-amino ketones prepared with good yields and characterized by IR, 1H, and 13C NMR Techniques.

S-(+) Camphorsulfonic Acid Glycine (CSAG) as Surfactant-Likes Brønsted Acidic Ionic Liquid for One-Pot Synthesis of ß-Amino Carbonyl

A rapid and efficient S-(+) camphor sulfonic acid Glycine (CSAG), catalyzed, one-pot three-component Mannich reaction has been performed to synthesize ß-amino carbonyl compound at room temperature. The reaction gave desired products in good yield and excellent diastereoselectivity. Products in the presence of CSAG (15 mol%) with yields of 52–89% were obtained. This method offers a new modification and easy working process in mild reaction conditions with a low amount and catalyst recyclability up to at least three periods without significant reduction in performance (efficiency 88–77%). This report describes for the first time the preparation of CSAG catalysts for the synthesis of Mannich products.

Polyaniline-Lemon Juice@Silica Nanocomposities an Efficient Catalyst for Synthesis of β-Amino Ketone

The lemon juice anchored polyaniline nanoparticles were synthesized using aniline as a monomer and lemon juice as acid dopant with potassium persulfate as the oxidant. The synthesized nanoparticles were characterized by XRD, FESEM and EDX. The XRD pattern of polyaniline-lemon juice has been shown crystalline nature and the average size found to be 2.998 nm. The polyaniline-lemon juice nanoparticles were immobilized on column silica by grinding method. The polyaniline-lemon juice@silica nanocomposite were characterized by XRD and FESEM. The XRD pattern of polyanilinelemon juice@silica nanocomposite has been shown amphorous nature. This study has explored the catalytic application of these nanocomposites in the synthesis of various β-amino ketones via a onepot three-component Mannich reaction of aldehydes, ketones and aromatic amines. This method provides a novel and enhanced amendment of three-component Mannich reaction in terms of mild reaction conditions and clean reaction profiles, using a small quantity of catalyst and simple workup procedure.

Organocatalytic enantioselective one-pot synthesis of β-aminoketones via Mannich reaction

An effective protocol for the asymmetric synthesis of β-amino carbonyl compounds using pyrrolidine based organocatalyst has been developed via one-pot three-component Mannich reaction. The organocatalyst (S)-N-(2,4-dinitrophenyl) pyrrolidine-2-carboxamide 3b confirmed to be the superior organocatalyst in solvent acetonitrile to obtain corresponding products in up to 89% yield and with excellent ee (90%). This organocatalytic reaction reveals productive result with a range of other aldehydes. Aromatic aldehydes having electron withdrawing substituent show the best results. Excellent yields, high enantioselectivity, mild reaction condition, and simple experimental work-up procedure are some of the advantages of this method.

Bi(NO3)3•5H2O-catalyzed Mannich Reaction: A Potent Catalyst for Synthesis of β-Aminocarbonyl Compounds

Biologically active compounds containing nitrogen, natural molecules and drugs are important for organic synthesis. Mannich reaction is one of the most common methods used for the synthesis of these compounds. Bi(NO3)3 was used as an efficient catalyst for the one-pot three-component Mannich reactions of ketones with different aromatic amines and aromatic aldehydes at room temperature. It is a good method to prepare β-amino carbonyl compounds in excellent yield. The high efficiency using simple starting materials and a catalytic amount of a reusable catalyst is especially noteworthy.

Nanostructured Zirconium Pyrophosphate Catalyzed Diastereoselective Synthesis of β-Amino Ketones via One-Pot Three-Component Mannich Reaction

In this study, ZrP2O7 catalytic nanomaterials were prepared by co-precipitation and polyvinylpyrrolidone assisted methods. These nanomaterials were structurally characterized by XRD, N2 adsorption/desorption, TGA, SEM and TEM microscopy techniques. This study investigated the application of these nanomaterials in the synthesis of various β-amino carbonyls via a one-pot-three-component condensation of aldehydes, ketones and amines. As a result, high efficiency was obtained in a water–ethanol mixed solvent at room temperature. Under the optimized conditions, the catalyst prepared via the PVP assisted method exhibited higher catalytic activity and higher diastereoselectivity when compared to the catalyst prepared by co-precipitation. Moreover, the ZrP2O7 catalysts were easily recovered and reused several times with only a slight loss of activity. At the conclusion of this study, a possible mechanism of the Mannich reaction over ZrP2O7 catalysts was also proposed and discussed.

Acid-ionic polymer as recyclable catalyst for one-pot three-component Mannich reaction

A recyclable solid-catalyst, acid-ionic polymer bearing imidazolium trifluoromethanesulfonate, [PS-Im][OTf] was presented as an efficient catalyst in a one-pot, three-component Mannich reaction of aldehydes, amines and ketones.

Deep eutectic solvent immobilized on SBA-15 as a novel separable catalyst for one-pot three-component Mannich reaction

An environmentally friendly and recyclable nanocomposite (HNMPCl/ZnCl2/SBA-15) was prepared by impregnation of N-methylpyrrolidonium-zinc chloride based deep eutectic solvent (HNMPCl/ZnCl2) on SBA-15. The catalytic activity of HNMPCl/ZnCl2/SBA-15 was investigated towards the one-pot three-component Mannich type reaction to a series of aldehydes, ketones, and amines and provided excellent activity and selectivity for the synthesis of β-amino ketones under mild reaction condition in green solvent. The HNMPCl/ZnCl2/SBA-15 was prepared using simple method from readily available starting material and was confirmed by FTIR, SEM, XRD, BET, and EDX. This protocol features green and efficient catalyst, ease of work up, simple separation without chromatography and reusability of the HNMPCl/ZnCl2/SBA-15 for four runs are the important highlights of this process, that it will find a wide variety of applications in academic and industrial research.

An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction

An environmentally friendly, photocontrollable and highly recyclable catalyst (ZrOPPAZOSO3H) has been synthesized by the immobilization of 4-[4-(6-phosphonic acid-hexanoxyl)phenylazo]benzenesulfonic acid onto zirconium phosphonate. This catalyst was characterized by Fourier transform infrared, scanning electron microscopy, X-ray powder diffraction, nitrogen adsorption-desorption and UV–vis analyses. The catalytic activity of ZrOPPAZOSO3H was investigated towards the one-pot three-component Mannich-type reaction of benzaldehyde, aniline and cyclohexanone in water at room temperature, and gave excellent yields. Interestingly, the catalytic activity could be regulated by photoirradiation. Furthermore, upon completion of the reaction, the product could be readily separated by extraction, and the water phase reused in the next run. Lastly, the catalyst could be readily recovered by centrifugation and reused up to six times without any discernible impact on its activity.

One-pot three-component kinetic controlled and syn-diastereoselective Mannich reaction of unfunctionalized ketones in water catalyzed by nano-manganese hydrogen sulfate particles

Direct catalytic three component Mannich reaction of aliphatic ketone, aldehyde and amine was described in the presence of a catalytic amount of nano-Mn(HSO4)2 (10 mol%) and a surfactant, for example sodium dodecyl sulfate (10 mol%) in the water as a green solvent. β-amino carbonyl compounds were obtained regioselectively as a less-substituted product from a one-pot three component Mannich reaction of 2-butanone in the above conditions. On the other hand, 3-pentanone as a symmetric ketone in the Mannich reactions gave β-amino carbonyl compounds with moderate to high syn diasterioselectivity. Control of regioselectivity and/or diasterioselectivity of the most products is related to micelle formation of organic substrates and SDS in water. Hydrophobic groups of substrates self-assembled in these microreactors whereas, hydrophilic groups were solvated with water or chelated with Mn(HSO4). The above interactions forwarded to these observed selectivity.

Mesoporous silica nanoparticles (MSNs) as an efficient and reusable nanocatalyst for synthesis of β-amino ketones through one-pot three-component Mannich reactions

In this paper, mesoporous silica nanoparticles (MSNs) are introduced as an efficient nanocatalyst for synthesis of β-amino ketones.

One-pot three-component Mannich reaction in water catalyzed by eco-friendly, hydrophobic and recyclable sulfonic acid based nanosilica (SBA-15-Ph-PrSO3H)

A mild, effective and green method for the Mannich reaction of aromatic aldehydes, aromatic amines and ketones has been accomplished in good to excellent yields using hydrophobic SBA-15-Ph-PrSO3H in water at room temperature.

PPh3-catalyzed Mannich reaction: a facile one-pot synthesis of β-amino carbonyl compounds under solvent-free conditions at room temperature

PPh3 was used as an efficient catalyst for the one-pot three-component Mannich reactions of acetophenone with different aromatic amines and aromatic aldehydes under solvent-free conditions at room temperature. This method provides a novel and improved method for preparing β-amino carbonyl compounds in the absence of acidic catalyst in excellent yield. Little catalyst loading, easy accessibility of the catalyst, mild conditions, and simple work-up procedure are the main features of this protocol.

H5CoW12O40@nanosilica: a green, bifunctional, heterogeneous nanocatalyst for one-pot three-component Mannich reaction in water

12-Tungestocobaltic acid, H5CoW12O40, was immobilized on nanosilica from rice husk ash to produce H5CoW12O40@nanosilica as a bifunctional nanocatalyst. The TEM result showed that the particles are mostly spherical in shape, and that they have an average size of approximately 10 nm. The catalytic activity of this catalyst was investigated in Mannich reaction of various aldehydes, ketones, and amines in water. This rapid procedure afforded structurally diverse β-amino ketones in high to excellent yields. Short reaction time, simple work-up procedure, elimination of toxic solvents, and low catalyst loading are the advantages of this procedure.

One-pot three-component Mannich reaction catalyzed by 2-hydroxylpyridine

An effcient synthetic protocol for the β-amino carbonyl compounds was developed via one-pot three-component Mannich reaction of aromatic aldehydes, aromatic amines and cyclohexanone catalyzed by 2-hydroxylpyridine under mild reaction conditions. β-Amino carbonyl compounds were obtained in moderate to good yields and reasonable diastereoselectivities. The effects of different solvents, catalyst amounts and the scope of different substrates on the Mannich reactions were investigated. The plausible reaction mechanism was also discussed.

Modification of poly(vinyl chloride) with pendant metal complex for catalytic applications

Abstract Poly(vinyl chloride) was modified to develop an alternative support for the preparation of polymer-supported catalysts. Commercially available poly(vinyl chloride) was synthetically modified to a polymer containing pendant primary amino groups. The Schiff-base of salicylaldehyde and the amino polymer were prepared and were used as the ligands in the synthesis of a polymer-supported copper complex. The polymer-supported ligand and catalysts were characterized by various physical methods. The polymer with the pendant copper complex was able to catalyze the one-pot three-component Mannich reaction between aldehydes, ketones and anilines under mild and environmentally friendly conditions. The catalyst can be recovered by simple filtration and is reusable.

A mild and efficient one-pot synthesis of $$\upbeta $$ -amino carbonyl compounds via Mannich reaction under ambient temperature condition

We have developed an efficient protocol for the synthesis of β-amino carbonyl compounds using phenylboronic acid as effective and eco-friendly catalyst via one-pot three-component Mannich reaction. Excellent yields, mild reaction condition, and simple experimental work-up procedure are some of the advantages of this method, which makes it a useful protocol for the synthesis of β-amino carbonyl compounds.

(±)-Camphor-10-sulfonic acid catalyzed direct one-pot three-component Mannich type reaction of alkyl (hetero)aryl ketones under solvent-free conditions: application to the synthesis of aminochromans

Direct three-component Mannich type reactions of (hetero)aromatic ketones with aromatic aldehydes and aromatic amines were efficiently catalyzed by camphor-10-sulfonic acid at ambient temperature under solvent free conditions to afford β-amino ketones in good to excellent yields. Syntheses of aminochromans were accomplished from one of the Mannich adducts via an unprecedented route involving intramolecular etherification with CuI/8-hydroxyquinoline.

Catalytic stereoselective Mannich reaction under solvent-free conditions

Abstract Silicon tetrachloride catalyzed one-pot three-component Mannich reaction of cyclic ketones, aromatic aldehydes, and aromatic amine under solvent-free conditions affords the corresponding β-amino ketones with excellent yield and good to excellent anti -selectivity.

Inorganic–organic hybrid silica based tin(II) catalyst: Synthesis, characterization and application in one-pot three-component Mannich reaction

Abstract Inorganic–organic hybrid material catalyzed one-pot three-component Mannich reaction of ketones with aromatic aldehydes and different amines at ambient temperatures afforded β-amino carbonyl compounds in excellent yields. This method provides a novel and improved modification of three-component Mannich reaction in terms of mild reaction conditions and clean reaction profiles, using small amount of catalyst, simple workup procedure and ease of recovery and reusability of catalyst.