Reaction Of Dimedone Research Articles

DABCO‐Saccharin Acetate as a Novel, Recyclable and Metal‐Free Catalyst for Eco‐Friendly Synthesis of Various Pyridazino[1,2‐a]indazole and 1H‐indazolo[1,2‐b]phthalazine Heterocycles Under Solvent‐Free Conditions

AbstractIn this research various pyridazino[1,2‐a]indazole and 1H‐indazolo[1,2‐b]phthalazine and 1H‐indazolo[1,2‐b]phthalazine derivatives were produced with a high yield via a multi‐component reaction of dimedone, aldehyde, hydrazine and anhydride compounds in the presence of a novel DABCO‐Saccharin acetate ([DABCOH][Sac‐CH3CO2]) ionic liquid under microwave irradiation. The applied method for producing these heterocyclic compounds demonstrated a number of desirable traits, including quick reactions, high yields of the final product, and straightforward separation of the product and catalyst from the reaction mixture.

Preparation and Characterization of Schiff Base Ligand Complexes (Dimedone With Thiourea)

In this study, eight complexes of this group were prepared by reacting the new ligand prepared from the reaction of dimedone with thiourea with metal chlorides of divalent (Mn, Co, Ni, Cu ,Zn, Cd) and trivalent (Fe, Cr) transition elements. These complexes were characterised by distinctive colours, melting points and solubility, and from the diagnostic results obtained, it was found that the ligand.(1E,5E)-5-carbamothioylimino)-3,3-dimethylcyclohexylidene) thiourea(L2) , that behave as dodecameric ligands with the metal ion, to which they bind through two amine groups. The octahedral shape of the complexes was suggested by IR, UV-visible, molar electrical conductivity, and magnetic susceptibility spectra, all of which indicated paramagnetic properties except for Zn and Cd, which have diamagnetic properties, and molar conductivity showed that all complexes are non-electrolytic except for Fe and Cr. The molecular formula of the complexes forming the group was determined by elemental analysis, where the elemental percentages matched the proposed molecular formula. The results measured the biological efficacy against pathogenic bacteria of the complexes showed varying efficacy. The results of antioxidant efficacy measurement using ethanol showed varying efficacy and were compared with gallic acid using DPPH as a free radical and gave different IC50 values. Density Functional Theory (DFT) measurement results showed that the chemical properties of the prepared complexes were consistent with the results of the practical part.

SO3H-Functionalized Epoxy-Immobilized Fe3O4 Core-Shell Magnetic Nanoparticles as an Efficient, Reusable, and Eco-Friendly Catalyst for the Sustainable and Green Synthesis of Pyran and Pyrrolidinone Derivatives.

A SO3H-functionalized epoxy-immobilized Fe3O4 core-shell magnetic nanocatalyst was prepared through a simple three-step procedure, and it was identified by various analyses such as Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), differential thermal gravity (DTG), Brunauer-Emmett-Teller (BET) analysis, transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX), thermogravimetric analysis (TGA), vibration sample magnetometry (VSM), and powder X-ray diffraction (PXRD). BET analysis showed that the as-prepared nanocatalyst was synthesized with a mesoporous structure and high specific area (35.45 m2 g-1). The TEM image clearly showed that the particle size distribution was in the range of 47-65 nm. The designed magnetic nanocatalyst was used successfully in the synthesis of pyran derivatives via the reaction of dimedone, malononitrile, and various aromatic aldehydes and synthesis of pyrrolidinone derivatives via the reaction of various aromatic aldehydes, aniline, and diethyl acetylenedicarboxylate. The nanocatalyst was simply isolated from the reaction mixture utilizing an external magnet and reused several times according to the model reactions without significant loss in its efficiency.

Bimetallic CoCeO2 oxide nanoparticles: An efficient and reusable heterogeneous catalyst for the preparation of 2‐amino‐3‐cyano‐4H‐pyran derivatives

AbstractCoCeO2 NPs were successfully synthesized and confirmed using x‐ray diffraction (XRD), field emission scanning electron microscopy (FESEM), and high‐resolution transmission electron microscopy (HRTEM) techniques. The catalytic performance of the synthesized CoCeO2 NPs catalyst was examined during the one‐pot multicomponent synthesis of biologically significant 2‐amino‐3‐cyano‐4H‐pyran derivatives. The reaction was easily accomplished using a one‐pot, three‐component reaction of dimedone, aryl aldehydes, and malononitrile in ethanol under reflux, with excellent yields and a short reaction time. The current catalytic system is more appealing because of its simple reaction conditions, uncomplicated product isolation, economic feasibility, and reusability of the catalyst free from significant loss of activity. This process offers an effective strategy for the synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives.

Synthesis and Characterization of some biologically active transition metal complexes for a ligand derived from dimedone with mixed ligands.

The aim of the work is synthesis and characterization of bidentate ligand
 [3-(3-acetylphenylamino)-5,5-dimethylcyclohex-3-enone][HL], from the
 reaction of dimedone with 3-amino acetophenone to produce the ligand
 [HL], the reaction was carried out in dry benzene as a solvent under reflux.
 The prepared ligand [HL] was characterized by FT-IR, UV-Vis
 spectroscopy, 'H, 8C-NMR spectra, Mass spectra, (C.H.N) and melting
 point. The mixed ligand complexes were prepared from ligand [HL] was
 used as a primary ligand while 8-hydroxy quinoline [HQ] was used as a
 secondary ligand with metal ion M(IT).Where M(IT) = (Mn ,Co ,Ni ,Cu ,Zn
 ,Cd and Pd) at reflux ,using ethanol as a solvent, KOH as a base.
 Complexes of the composition [M(L)(Q)] with (1:1:1) molar ratio were
 prepared . All the complexes were characterized by spectroscopic methods
 (FT-IR, UV-Vis spectroscopy) along with elemental analysis (A.A),
 chloride content and melting point measurements were carried out, together
 with conductivity and magnetic susceptibility. These measurements showed
 tetrahedral geometry around (Mn", Col, Ni, Cu", Zn! and Cd") ions and
 square planner around (Pd") ion. The biological activity of the ligands
 [HL],[HQ] ] and complexes (MLQ): were studied using inhibition method.

Reactions of dimedone and alkyl orthoformates with and without activators

Reactions of dimedone and alkyl orthoformates with and without activators

A Novel Recyclable Bi-Mg-O Composite Nano-Catalyst Promoted Rapid and Efficient Synthesis of Spirooxindole and 4H-Pyran Derivatives

A novel Bi-Mg-O composite nano-catalyst was prepared by using Bi(NO3)3 and nano-MgO. Prepared catalyst was characterized using x-ray diffraction (XRD) analysis, scanning electron microscope (SEM), X-ray photoelectron spectroscopy (XPS) technique which confirms its nano-crystalline nature and composition. The synthesized novel catalyst Bi-Mg-O was found to be competent catalyst for the synthesis of spirooxindole derivatives by multicomponent reaction of isatin, dimedone, malononitrile and 4H-pyran derivatives by reaction of dimedone, aryl aldehydes and malononitrile using ethanol as solvent at room temperature. The nanocatalyst proved to be recyclable as it is recycled and recovered for three runs without notable loss in catalytic activity. All synthesized derivatives were obtained in exemplary yields. Novel recyclable nanocatalyst, good yields of products, and benign reaction conditions are the noteworthy aspects of the present protocol.

Functionalization of magnetic nanoparticles by creatine as a novel and efficient catalyst for the green synthesis of 2-amino-4H-chromene derivatives

By employing the naturally-originated molecule of creatine, Fe3O4@SiO2-creatine as an environmentally benign magnetic organometallic nanobiocatalyst was successfully prepared via a convenient and green route. Then to acquire an inclusive comprehension of different properties of the catalyst, it was studied by various characterization techniques such as FT‐IR, FE-SEM, TEM, EDX, XRD, and VSM analyses. It was found that the size distribution of nanoparticles was an average diameter size of 70 nm. To examine the catalytic activity, it was applied in sequential knoevenagel condensation-Michael addition room temperature reaction of dimedone, malononitrile, and different substituted aromatic aldehydes to produce a variety of 2-amino-tetrahydro-4H-chromene-3-carbonitrile derivatives in a single step. Among the multiple outstanding advantages that can be mentioned for this work, some of the most noticeable ones include: affording the products in short reaction times with high yields, operating the reaction at ambient conditions and ease of catalyst separation.

Grinding Synthesis of 2‐Amino‐4H‐benzo[b]pyran Derivatives Catalyzed By Highly Efficient GPTMS/Guanidine Protected Magnetic Nanoparticles**

AbstractIn this study, we synthesized the GPTMS‐guanidine attached to the magnetic nanoparticles (Fe3O4@SiO2@GPTMS@guanidine) as a novel and efficient heterogeneous nanocatalyst through cheap and available materials. Then, the Fe3O4@SiO2@GPTMS@guanidine nanoparticles were characterized by various analyses such as fourier transform infrared spectroscopy (FT‐IR), thermogravimetric analysis (TGA), X‐ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy‐dispersive X‐ray spectroscopy (EDX), vibrating sample magnetometry (VSM), and Brunauer–Emmett–Teller (BET). The Fe3O4@SiO2@GPTMS@guanidine nanoparticles were used for the effective and green synthesis of 2‐amino‐4H‐benzo[b]pyran derivatives by grinding method through one‐pot three‐component reactions of dimedone, various aromatic aldehydes and malononitrile at room temperature. Moreover, the reaction in the water as green solvent was checked and acceptable results were obtained. The benefits of these methods include reusability of the Fe3O4@SiO2@GPTMS@guanidine, easy purification, and synthesis of derivatives with high yields and short reaction time. The catalyst has the ability to react up to at least 9 times, without a significant reduction in its activity.

Ultrases Destekli 9-(Substitue heteroaril) akridindion Türevlerinin Tek Basamakta Sentezi

An efficient green approach for the synthesis of 9-heteroaryl-acridine-1,8-dione derivatives (3a-f) was accomplished via reactions of dimedone (1) with various heteroaromatic aldehydes (2a-f) and ammonium acetate through one-pot multicomponent reactions in water under mild conditions using ultrasound irradiation in excellent yields. Of the synthesized compounds, 3d-f were novel and this process presents the advantages of high yields and easy work-up procedures. Spectral analyses were accomplished by FTIR, 1H NMR, 13C NMR and LC-MS TOF analyses.

Synthesis of Fused Azo-linked Acridine Derivatives Using MCM-41/Ag2S-RHA Nanocomposite.

In this study, the synthesis of azo-linked acridine by the reaction of dimedone and synthesized diazoaryl-(2-amino-5-(phenyl)methanone using Ag2S/RHA-MCM-41nanocomposite is reported. The synthesized catalyst was characterized by FT-IR, XRD, and SEM. According to the obtained results, Ag2S/RHA-MCM-41 nanocomposite exhibited high activity in the synthesis of azo-acridine derivatives based on desirable yields and reaction time. Products were prepared in 1.5-2 h and with 88-93% yield. In all the reactions, the catalyst could be easily removed and reused, and its catalytic activity was maintained after five uses and did not decrease significantly. The structures of all newly synthesized products were characterized by spectroscopic spectra (FT-IR, 1H NMR, 13C NMR) and elemental analyses. The results of the study showed that ionic liquid [DBU]OAc (entry 8) and MCM- 41/Ag2S-RHA nanocomposite (entry 8) possessed better efficiency and shorter time than other reaction conditions. In this study, new azo-linked acridine derivatives were synthesized by the reaction of different azo derivatives and dimedone using MCM-41/Ag2S-RHA nanocomposite, and the reaction products were obtained in 1.5-2 h with an efficiency of 88-93%. The short reaction time and high efficiency of the obtained products indicated the high efficiency of this method. In all the reactions, MCM-41/Ag2S-RHA nanocomposite could be easily removed and reused. Its catalytic activity was maintained in the sample reaction after five runs and did not decrease significantly.

Synthesis of Novel fused Azo-linked acridine derivatives using GO-ZnO nanocomposite

In this study, the synthesis of novel azo-linked acridines via the reaction of dimedone and synthesized diazoaryl-(2-amino-5-(phenyl)methanone using GO-ZnO nanocomposite is reported. The synthesized catalyst was characterized by FT-IR, XRD, UV-Visible, TEM and SEM. According to the results, Graphene Oxid-ZnO (GO-ZnO) nanocomposite revealed high activity in the synthesis of azo-acridine derivatives. In all reactions, the catalyst can be easily removed and is reusable. The catalytic activity of GO-ZnO is maintained after five runs without significant decrease. The structures of all new synthesized products were characterized by spectroscopic data (FT-IR, 1H NMR and 13C NMR) and elemental analyses.

5-Aminopyrazole-4-carbonitriles as precursors to novel 4-aminotetrahydropyrazolo[3,4-b]quinolin-5-ones and N-(4-cyanopyrazol-5-yl)pyridine-3-carbonitrile

We report an efficient synthesis of 4-aminotetrahydropyrazolo[3,4-b]quinolin-5-one derivatives via Friedländer-type reaction of dimedone with 5-aminopyrazole-4-carbonitriles in the presence of an acidic catalyst. We also report the synthesis of N-(1H-pyrazol-5-yl)- pyridine-3-carbonitrile via the reaction of pyrazol-5-ylcyanoacetamide with acetylacetone in the presence of basic catalyst.

Efficient solvent free synthesis of tetrahydrobenzo[a]xanthene-11-one derivatives using nano-AlPO4/Ti (IV) as a green, heterogeneous and reusable catalyst

A new green protocol has been developed for synthesis of tetrahydrobenzo[a]xanthen-11-ones via a three component, one-pot condensation reaction of dimedone, β-naphthol and aromatic aldehydes using nano-AlPO4/Ti (IV) (NAP-Ti(IV)) as a reusable and novel catalyst at 90 °C under solvent-free condition. Short reaction times, high yields, scale up and easy work-up are advantages of this protocol. The prepared nano-AlPO4/Ti(IV) was fully characterized by EDX, XRD, SEM, IR analysis. The obtained tetrahydrobenzo[a]xanthen-11-ones were characterized by various methods such as FT-IR, 1HNMR.

Advancement in synthetic strategies of bisdimedones: Two decades study

AbstractBisdimedones have emerged as an important and versatile moiety in the field of synthetic and medicinal chemistry. It is screened as a precursor for the synthesis of several heterocycles such as acridinediones, xanthenediones, thioxanthenes, and benzopyrans that exhibited immense pharmacological as well as industrial applications. Its extensive characteristics have attracted the scientists to develop various protocols for the synthesis of bisdimedones and their derivatives from the reaction of dimedone with several aldehydes under different environmental conditions using various types of catalysts. This review encapsulates the recent progress in the synthesis of bisdimedone derivatives under several reaction protocols such as the use of nanoparticles, ionic liquids, metal salts, simple organic compounds, and catalyst‐free conditions, and so forth in the last 20 years.

Bi Metal-Organic Framework (Ce/Ni-BTC) as Heterogeneous Catalyst for the Green Synthesis of Substituted Chromeno[4, 3-b]quinolone under Solvent Free Condition.

Novel bi metal organic framework (b-MOF) is synthesized and used as a heterogeneous catalyst for the synthesis of chromeno[4, 3-b]quinolone derivatives via one-pot and solvent-free, four-component reaction of dimedone, aromatic aldehydes, 4-hydroxycoumarin and ammonium acetate at 110°C. b-MOFs can be used as a heterogeneous catalyst in the synthesis of many organic compounds. The active and multi-purpose sites in b-MOFs provide a varied function in their catalytic applications. In this paper, reductive CES method is applied for the synthesis of Ce0.47/Ni0.53-BTC b-MOF. The resulting b-MOF was used as a heterogeneous catalyst for the synthesis of chromeno[4, 3-b]quinolone via one-pot and solvent-free, fourcomponent reaction of dimedone, aromatic aldehyde, 4-hydroxycoumarin and ammonium acetate at 110 °C. Ce0.47/Ni0.53-BTC was synthesized in an electrochemical cell composed of a stainless steel foil with a size of 5cm×5cm centered between two 5cm×5cm sized graphite plates as the anodes by the cathodic current density of 0.2 A/dm2 and placed in a solution of cerium nitrate (0.3 g), nickel nitrate (0.3 g), H3BTC (0.2 g) and NaNO3 (0.1 g) in ethanol (500 mL). Ce0.47/Ni0.53-BTC (10 mg) was added to a mixture of dimedone (1 mmol), aromatic aldehyde (1 mmol), hydroxycoumarin (1 mmol) and ammonium acetate (1.5 mmol) and stirred at 110 °C under solvent-free conditions for 45 min. The reaction evolution was controlled by the TLC (hexane:ethyl acetate, 4:1). Then, boiling ethanol was added to the reaction mixture and stirred at room temperature for 15 min. After the reaction completion, the catalyst was separated by centrifuge. Finally, the reaction mixture was placed in an ice bath, which resulted in a white solid product and recrystallized from ethanol to give the pure product. The b-MOF catalyst showed very good efficiency in the synthesis of the desired compounds and can be easily recovered by centrifuge and reused at least five times without a decrease in catalytic activity. In this report, a novel bi metal-organic framework (Ce0.47/Ni0.53-BTC) is synthesized via the cathodic electrosynthesis method. The synthesized b-MOF is fully characterized by several characterization methods. The catalytic activity of Ce0.47/Ni0.53-BTC is investigated in the synthesis of chromeno[4, 3-b]quinolone derivatives via one-pot four-component reaction of dimedone, aromatic aldehyde, 4-hydroxycoumarin and ammonium acetate. The reaction optimization results showed that the highest isolated yield was obtained when the reaction was performed in solvent-free conditions at 110 °C. The catalyst showed to be highly efficient in the synthesis of the desired compounds and performing the reaction utilizing various starting materials gave the products in good isolated yields, which proves the generality and the scope of the method. The catalyst could easily be recovered by centrifuge and reused at least five times without a decrease in catalytic activity.

Ultrasound assisted regioselective synthesis, photophysical and structural studies of 1-substituted indazol-4(5H)-ones and enaminodiketones of dimedone

Enaminodiketone, obtained from reaction of dimedone with DMF-DMA, on reaction with nucleophiles such as amines, guanidine hydrochloride and substituted aromatic hydrazines furnished enaminodiketones, quinazolines and indazole derivatives respectively. The structure of synthesised compounds was assigned on the basis of spectral data (IR, NMR and Mass). X-ray crystallographic studies of representative compound 6b have been reported. DFT studies were carried out on indazole derivative and its regioisomer for validation of the assigned structure. Also experimental NMR is correlated with that obtained from theoretical studies. Photo physical (UV and fluorescence) studies of compounds 4 and 6 have also been reported.

Electrochemical synthesis of three‐dimensional flower‐like Ni/Co–BTC bimetallic organic framework as heterogeneous catalyst for solvent‐free and green synthesis of substituted chromeno[4,3–b]quinolones

AbstractIn this research, a new flower‐like Ni0.77/Co0.23– benzene–1,3,5–tricarboxylate (BTC) bimetallic organic framework (Ni/Co–BTC BMOF) is synthesized via the cathodic electrosynthesis (CE) method, based on nickel and cobalt metals and BTC linker. The synthesized BMOF is characterized by several methods, including Fourier transform infrared spectroscopy (FT‐IR), powder X‐ray diffraction (PXRD), field emission scanning electron microscopy (FE‐SEM), and energy dispersive X‐ray analysis (EDX). The catalytic activity of the resulting Ni/Co is evaluated in a one‐pot four‐component reaction of dimedone, aromatic aldehyde, 4–hydroxycoumarin, and ammonium acetate for the synthesis of chromeno[4,3–b]quinolone derivatives under solvent‐free condition. The Ni/Co–BTC BMOF catalyst showed very good activity in the tested reaction, and a wide scope of starting materials gave the desired products in high isolated yields in the presence of the Ni/Co–BTC BMOF catalyst. The recovery of Ni/Co BMOF was achieved by a centrifuge, and it was reused at least six times without any significant decrease in catalytic activity.

Features of the Reaction of Dimedone with Some Amines in the Presence of Mercury(II) Acetate

Regiochemistry of the reaction of N-substituted propargylamines with dimedone in the presence of mercury(II) acetate was studied. Xanthene and diene derivatives, as well as symmetric mercury aminopropinides, were obtained, for one of which the crystallographic parameters are given.

Nano-cerium Oxide/Aluminum Oxide: An Efficient and Useful Catalyst for the Synthesis of Tetrahydro[a]xanthenes-11-one Derivatives

Tetrahydro[a]xanthenes-11-one derivatives have been widely used industrially as agrochemicals, cosmetics and pigments are reported to exert broad spectrum biological and pharmacological activities. Herein, we reported an efficient and environmentally benign one-pot multi–component reaction for the synthesis of tetrahydro[a]xanthenes-11-one derivatives from the reaction of dimedone, aromatic aldehydes, and 2-naphthols in the presence of a catalytic amount of nano-nano-CeO2/Al2O3. The advantages of the effective method included good yields (91-98%), short reaction times, simple work-up and reusable catalyst. The catalyst could be recycled and reused for five times without much loss in its activity.