Three-component Reaction Of Dimedone Research Articles

β-cyclodextrin: Green catalyst for the efficient and expeditious synthesis of benzodiazepines under aqueous conditions

An efficient and facile green method for synthesis of four substituted 1,5-benzodiazepine derivatives via a three-component reaction of dimedone, o-phenyl diamine, and various substituted aldehydes are designed using β-cyclodextrin as a catalyst at reflux condition. The current one-pot multicomponent methodology offers several advantages, such as good to excellent yields, simplicity in experimental procedure, easy work-up procedure, shorter reaction time, energy-conserving, broad substrate scope, avoidance of hazardous chemicals, etc. Further, the catalyst was recovered and recycled 4–5 times without compromising the yield of the final product.

Synthesis of tetracyclic pyrido-fused dibenzodiazepines via a catalyst-free cascade reaction.

An efficient, eco-friendly protocol has been described for the chemoselective synthesis of tetracyclic pyrido-fused dibenzodiazepines derivatives via catalyst-free, three-component reaction of dimedone, 1,2-diamines, 3-formylchromones, and malononitrile. The significant advantages of this cascade approach are to create two new rings and four new σ bonds containing three C-N and one C-C bond, as well as the breakdown of a C-O bond.

Triethanolamine lactate-supported nanomagnetic cellulose: a green and efficient catalyst for the synthesis of pyrazolo[3,4-b]quinolines and theoretical study

A novel nanomagnetic catalyst has been synthesized by immobilization of triethanolamine lactate cellulose with Fe3O4 NPs. The prepared catalyst has been used as an efficient and recoverable catalyst for the regioselective synthesis of pyrazolo quinolones by the three-component reaction of dimedone, 5-amino pyrazolone and aromatic aldehydes in ultrasound condition. This economical catalyst provides high yields of products, short experimental time and easy workup for green synthesis of pyrazolo[3,4-b]quinolone compounds. Theoretical studies have been employed to investigate the reaction mechanism by using the B3LYP/6-311G method. Electronic parameters of all components have been determined in order to reorganize the role of components in the reaction mechanism.

Three-Component Reaction of Dimedone with Aromatic Aldehydes and 5-Aminotetrazole

Reactions of dimedone with aromatic aldehyde and 5-aminotetrazole monohydrate proceeded with the formation of 9-aryl-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazoline-8(4H)-ones or 9-aryl-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-diones depending on the nature of substituent in aromatic aldehyde. Antimicrobial, antifungal and analgesic activities of the synthesized compounds were studied.

Mesoporous SBA-15/PIDA as a Dendrimer Zwitterionic Amino Acid-Type Organocatalyst for Three-Component Indazolophtalazine Synthesis

A zwitterionic amino acid-like N-propyliminodiacetic acid (PIDA) organocatalyst supported to a heterogeneous surface (SBA-15/PIDA) based on iminodiacetic acid and mesoporous SBA-15, respectively was synthesized. The mesoporous hybrid catalyst was successfully characterized by SEM, TEM, TGA, FTIR, and EDS and employed in the three-component reaction of dimedone, aldehydes and phtalhydrazide for the synthesis of indazolophtalazinetrione. SBA-15/PIDA exhibited excellent catalytic activity in the reaction and showed highly recyclable and recoverable features in consecutive reaction runs. According to ab initio calculations, the recoverability of SBA-15/PIDA catalyst is attributed to the strong covalent bonding between PIDA and SBA-15.

ChemInform Abstract: Convenient Synthesis of Functionalized 3,4,10,11‐Tetrahydroindolo[1,2‐a]quinoxalines via Three‐Component Reaction of Dimedone, 3‐Nitrochromenes and Ammonium Acetate.

An efficient synthetic procedure for the functionalized 3,4,10,11-tetrahydroindolo[1,2-a]quinoxalines was successfully developed by the three-component reaction of dimedone, 3-nitrochromenes, and ammonium acetate in ethanol. This reaction has the advantages of using common starting material, short reaction process, and good yields high-atom efficiency.

Cyclodextrin nanosponges: a potential catalyst and catalyst support for synthesis of xanthenes

The nanoporous framework of a cyclodextrin nanosponge was used as catalyst for accelerating the one-pot, three-component reaction of dimedone, aldehyde, and phenols for synthesis of xanthene derivatives. Moreover, the nanocavities of cyclodextrin nanosponges were exploited for immobilization of heteropolyacids through the wet impregnation method. This catalyst exhibited superior catalytic performance compared to the bare cyclodextrin nanosponge. Despite the good catalytic activity, the leaching of the catalytic species did not allow efficient recovery and reusability. To circumvent this problem, the cyclodextrin nanosponge was amine-functionalized prior to heteropolyacid immobilization. The results proved that the amine functionalities had an effective role in preserving the catalytic species and improving the reusability through decreasing the leaching time. This catalyst was used for synthesis of a variety of xanthenes in aqueous media. The catalytic amount of catalyst afforded the desired product in excellent yields and with a relatively short reaction time. The results suggested cyclodextrin nanosponge-based catalysts as potential candidates for promoting chemical reactions.

An Efficient One-Pot Two-Step Three-Component Process for the Synthesis of Trifluoromethylated Hydrochromenes

A one-pot two-step three-component process for the synthesis of trifluoromethylated 2-hydroxy-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromenes has been developed. The three-component reaction of dimedone, substituted benzaldehydes, and methyl 4,4,4-trifluorobut-2-ynoate gave the desired products in moderate to good yields. Excellent regioselectivity and diastereoselectivity were observed. Furthermore, refluxing the product chromenes with p-toluenesulfonic acid in toluene gave the corresponding dehydrated products – trifluoromethylated 5-oxo-5,6,7,8-tetrahydro-4H-chromenes.

Fe3O4@silica Sulfonic Acid Nanocomposite as a Magnetically Separable Catalyst for the Synthesis of 2-Arylpyrrolo[2,3,4-kl]Acridin-1(2H)-Ones

The synthesis of a series of 2-arylpyrrolo[2,3,4-kl]acridin-1(2H)-ones, three of which are novel, though a one-pot three-component reaction of dimedone, various anilines, and isatin has been achieved in the presence of magnetite nanoparticles supported silica-sulfonic acid as catalyst under solvent-free conditions at 80 °C. The procedure avoids hazardous reagents/solvents and is more eco-friendly than existing methods. Fe3O4@silica-sulfonic acid is shown to be a highly efficient catalyst, and could be readily recovered using a simple external magnet and reused several times without any significant loss in activity. The catalyst was fully characterised by FTIR, SEM, XRD, EDX and VSM.

One-pot, three-component reaction of dimedone, amines, and isatin in the presence of tris(hydrogensulfato) boron: synthesis of pyrroloacridine derivatives

A one-pot, three-component reaction of dimedone, anilines. and isatin has been described leading to the synthesis of 2-arylpyrroloacridin-1(2H)-ones in the presence of tris(hydrogensulfato) boron [B(HSO4)3] at reflux in ethanol. However, in the cases of aliphatic amines, tetrahydroxanthene has been obtained from the reaction of isatin and dimedone.

Ultrasound-assisted three-component synthesis of 3-(5-amino-1 H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones in water

Indium(III) chloride was found to be an efficient catalyst for the synthesis of 3-(5-amino-1 H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones by one-pot, three-component reaction of dimedone, 1 H-pyrazol-5-amines and isatins in water under ultrasonic irradiation. The advantages of this method are the use of a readily available catalyst, easy workup, excellent yields, and the use of water as a solvent that is considered to be relatively environmentally benign.