Synthesis Of Tetrahydrobenzo Research Articles

Tri-vanadium Substituted Dawson-type Heteropolytungstate Nanocomposite (g-C3N4/Fe3O4@P2W15V3) as a Novel, Green, and Recyclable Nanomagnetic Catalyst in the Synthesis of Tetrahydrobenzo[b]Pyrans

Among the important needs of human societies are the reduction of biological pollution and the use of environmentally friendly and inexpensive solvents. For the synthesis of medicinally important heterocycles, there is a need for an easy, efficient, and environmentally friendly catalytic protocol through multicomponent reaction (MCR). In this regard, the construction of multi-functional composites has been considered. A novel magnetic graphite carbon nitride decorated by tri-vanadium substituted Dawson-type heteropolytungstate nanocomposite (C3N4/Fe3O4@P2W15V3) effectively synthesized and characterized by prevalent functional analysis. This heterogeneous catalyst produced various tetrahydrobenzo[b]pyran derivatives in the presence of ethanol as a green solvent. Among the advantages observed for this method is the presence of a heterogeneous and reusable catalyst that is easily isolated and provides a high yield of products in a very short reaction time with high purity.

Synthesis of Tetrahydrobenzo[b]pyrans Promoted by Sodium Stearate as a Lewis Base-Surfactant Combined Catalyst in an Aqueous Micellar Medium

Synthesis of Tetrahydrobenzo[b]pyrans Promoted by Sodium Stearate as a Lewis Base-Surfactant Combined Catalyst in an Aqueous Micellar Medium

The Immobilized Zirconocene Chloride on Magnetite‐reduced Graphene Oxide: A Highly Efficient and Reusable Heterogeneous Nanocatalyst for One‐pot Three‐component Synthesis of Tetrahydrobenzo[b]pyrans and Dihydropyrano[3,2‐c]chromenes

AbstractThe present paper describes the synthesis and characterization of the functionalized magnetite reduced graphene oxide (rGO@Fe3O4) with zirconocene dichloride as rGO@Fe3O4@ZrCp2Cl2. The prepared magnetic nanomaterial was characterized by Fourier‐transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), energy‐dispersive X‐ray spectroscopy (EDX), X‐ray diffraction (XRD), thermogravimetric analysis (TGA), vibrating sample magnetometer (VSM), inductively coupled plasma optical emission spectroscopy (ICP‐OES) and mass spectrometry (MS). This new heterogeneous nanocatalyst showed the perfect catalytic activity towards synthesis of tetrahydrobenzo[b]pyran and Dihydropyrano[3,2‐c]chromenes derivatives through multicomponent reaction of dimedone or 4‐hydroxycoumarin, malononitrile and aromatic aldehydes in polyethylene glycol 400 (PEG‐400) at 100 °C. The influence of the amount of nanocatalyst, varying temperature of the reaction and the kind of solvent on the rate of condensation reaction was investigated. Recovery and reusability of the applied nanocatalyst was examined for five consecutive cycles without the significant loss of its catalytic activity.

Green Approach for Metal-free One-pot Synthesis of Tetrahydrobenzo[b]pyrans with Sodium Alginate as a Reusable Bifunctional Biopolymeric Catalyst

Green Approach for Metal-free One-pot Synthesis of Tetrahydrobenzo[b]pyrans with Sodium Alginate as a Reusable Bifunctional Biopolymeric Catalyst

P-TSA Catalyzed Synthesis of Tetrahydrobenzo[g]quinolines via Multicomponent Reaction using Pyrazole Aldehyde, Lawsone, β-Ketoesters and Ammonium Acetate

An efficient protocol has been developed for the multicomponent synthesis of tetrahydrobenzo[g]quinoline-3-carboxylate derivatives using p-toluenesulfonic acid (p-TSA) as catalyst through one-pot four component condensation reaction of pyrazole aldehyde, Lawsone, β-ketoesters and ammonium acetate in ethanol. The synthesized compounds were characterized by spectroscopic techniques.

Fe3O4–SiO2–Bi2O3-catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives Under Solvent-Free Conditions

Fe3O4–SiO2–Bi2O3-catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives Under Solvent-Free Conditions

Solar Energy Mediated Green Synthesis of Tetrahydrobenzo[b]pyrans Using L-Ascorbic Acid as an Organocatalyst in Aqueous Medium

A major theme in modern organic synthesis is the development of greener and more ecofriendly protocols, often entraining multicomponent reactions (MCRs) for their simplicity and atom economy. Such ...

Synthesis of Tetrahydrobenzo[b]thiophene-3-carbohydrazide Derivatives as Potential Anti-cancer Agents and Pim-1 Kinase Inhibitors.

Tetrahydrobenzo[b]thiophene derivatives are well known to be biologically active compounds and many of them occupy a wide range of anticancer agent drugs. One of the main aim of this work was to synthesize target molecules not only possessing anti-tumor activities but also kinase inhibitors. To achieve this goal, our strategy was to synthesize a series of 4,5,6,7- tetrahydrobenzo[b]thiophene-3-carbohydrazide derivatives using cyclohexan-1,4-dione and cyanoacetylhydrazine to give the 2-amino-6-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbohydrazide (3) as the key starting material for many heterocyclization reactions. Compound 3 was reacted with some aryldiazonium salts and the products were cyclised when reacted with either malononitrile or ethyl cyanoacetate. Thiazole derivatives were also obtained through the reaction of compound 3 with phenylisothiocyanate followed by heterocyclization with α-halocarbonyl derivatives. Pyrazole, triazole and pyran derivatives were also obtained. The compounds obtained in this work were evaluated for their in-vitro cytotoxic activity against c-Met kinase, and the six typical cancer cell lines (A549, H460, HT-29, MKN-45, U87MG, and SMMC-7721). The results of anti-proliferative evaluations and c-Met kinase, Pim-1 kinse inhibitions revealed that some compounds showed high activities. The most promising compounds 5b, 5c, 7c, 7d, 11b, 14a, 16b, 18b, 19, 21a, 23c, 23d and 23i against c-Met kinase were further investigated against the five tyrosin kinases (c-Kit, Flt-3, VEGFR-2, EGFR, and PDGFR). Compounds 5b, 5c, 7d, 7e, 11b, 11c, 16c, 16d, 18c, 19, 23e, 23k and 23m were selected to examine their Pim-1 kinase inhibitions activity where compounds 7d, 7e, 11b, 11c, 16d, 18c and 23e showed high activities. All of the synthesized compounds have no impaired effect toward the VERO normal cell line.

Graphene Oxide Functionalized Organic-Inorganic Hybrid (GO–Si–NH2–PMo): An Efficient and Green Catalyst for the Synthesis of Tetrahydrobenzo[b]pyran Derivatives

In this study, a graphene oxide (GO) functionalized organic-inorganic hybrid was prepared by covalently immobilization of organic (3-aminopropyltrimethoxysilane) and inorganic (H3PMo12O40) groups on the basal plane of GO. Structure of catalyst was characterized with different analysis such as FT-IR, SEM, TEM, EDS, WDX, XRD, and TGA. All analyses approve the successful covalently immobilization of organic and inorganic parts on the GO. The activity of catalyst has been tested for the synthesis of tetrahydrobenzo[b]pyran derivatives under solvent-free condition in short reaction time and good to excellent yields. Highlights Efficient synthesis of tetrahydrobenzo[b]pyran derivatives Green and heterogeneous organic and inorganic hybrid catalyst Preparation of a graphene oxide functionalized heteropolyacid Reusable catalyst for at least for 5 runs

LaMnO3 Supported Ionic Liquid; an Efficient Catalyst for One-Pot Three-Component Synthesis of Tetrahydrobenzo[b]Pyran Derivatives Under Solvent-Free Conditions

A new recyclable nanocatalyst consisting of heteropoly acid grafted on ionic liquid modified LaMnO3 nanoparticles was synthesized and accomplished as an efficient catalyst in condensation reaction for the preparation of tetrahydrobenzo[b]pyrans under solvent-free conditions. In addition, it was clarified that supported heteropoly acid (HPA) is the active site for the catalytic reaction, whereas the LaMnO3, ionic liquid functionalized lanthanum manganite nanoparticles are inactive. Different physicochemical methods such as Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), and field emission scanning electron microscopy (FESEM) were used to characterize the hybrid nanomaterial. The nanocatalyst reusability was affirmed by the use of five consecutive runs. Compared with the various previously reported catalyst, the new synthesized catalyst was found to be the most efficient with regard to reaction time, yield and ease of catalyst separation.

Synthesis of Tetrahydrobenzo[a]xanthen-11-ones Catalyzed byAcid Ionic Liquid Functionalized β-Cyclodextrin in Water

Synthesis of Tetrahydrobenzo[a]xanthen-11-ones Catalyzed byAcid Ionic Liquid Functionalized β-Cyclodextrin in Water

Recent Advances in Three-Component Cyclocondensation of Dimedone with Aldehydes and Malononitrile for Construction of Tetrahydrobenzo[b]pyrans Using Organocatalysts

Background: The majority of naturally occurring compounds, pharmaceuticals, and drug-candidate molecules possess heterocyclic scaffolds. In this context, tetrahydobenzo[b]pyrans are of considerable importance. In the line with the synthesis of these valuable heterocyclic compounds, the researchers tried to synthesize these molecules using different organocatalysts. The development of new strategies for three-component condensation of dimedone, various aldehydes and malononitrile for construction of tetrahydrobenzo[b]pyrans is of particular interest to organic chemists and pharmacologists. Objective: In this review, three-component catalyzed synthesis of tetrahydrobenzo[b]pyran compounds is introduced, focusing on the developments in the use of organocatalysts. Organocatalytic approaches were investigated for the synthesis of tetrahydrobenzo[b]pyrans. This contribution covers the literature concerning the synthesis of heterocycles referred to, in recent times. Conclusion: This review article is associated with the study of the three-component synthesis of tetrahydrobenzo[b]pyrans using organocatalysts. This review also provides an insight into the importance of these heterocycles. In the vast majority of these reactions, water and water-ethanol system have been used as green solvent media for implementation of them. The use of green solvents, the development of less toxic and promising reagents/catalysts as well as the design of inexpensive and reliable approaches are some of the principles of green chemistry, and most of the methods are benefited from them. Tetrahydrobenzo[b]pyrans and organocatalysts open avenue ofnew horizons. The recyclability of the many of these organocatalysts offers an additional merit for the use of these catalysts in 3-CR of aldehydes, dimedone, and malononitrile reactions.

Trichloroisocyanuric Acid as a Highly Efficient Catalyst for the Synthesis of Tetrahydrobenzo[b]pyran Derivatives

Tetrahydrobenzo[b]pyran derivatives are an important class of heterocyclic compounds due to their biological and pharmacological activities, such as anticancer, anticoagulant, diuretic, spasmolytic...

Synthesis of Tetrahydrobenzo[B]Pyran Derivatives Using Thiamine Hydrochloride (VB1) : A Green Catalyst

Synthesis of Tetrahydrobenzo[B]Pyran Derivatives Using Thiamine Hydrochloride (VB1) : A Green Catalyst

Synthesis of Tetrahydrobenzo[g]Quinoline Derivatives Using Recoverable Carbonaceous Material as Heterogeneous Catalyst

A variety of substituted benzo[g]quinoline‐5,10‐dione derivatives were synthesized via one‐pot three‐component reaction of 2‐hydroxynaphthalene‐1,4‐dione, aromatic aldehydes, and (E)‐3‐aminobut‐2‐enoates using carbonaceous material as the heterocyclic catalyst. This procedure is simple and efficient owing to short reaction times, easy work‐up, and recovery of heterogeneous catalyst. This procedure develops an efficient and promising synthetic method to construction of the benzo[g]quinoline‐5,10‐dione skeleton.

Synthesis of Fe 3 O 4 /Eggshell Nanocomposite and Application for Preparation of Tetrahydrobenzo[b]Pyran Derivatives

This work is reported on the synthesis of Fe3O4/eggshell nanocomposites in the absence of any stabilizer or surfactant. Fe3O4 magnetic nanoparticles were established on the egg shell nano-composite. The nanocompositeshave shown high catalytic activities in the synthesis of Tetrahydrobenzo[b]pyran. These derivatives were synthesized via an one‐pot three‐component condensation of aromatic aldehydes with malononitrile and dimedonewith excellent yields in the presence of Fe3O4/eggshell nanocomposites as a highly efficient heterogeneous catalyst. The obtained catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), Field emission scanning electron microscopy (FE-SEM), X-ray diffraction analysis (XRD) and Vibrating sample magnetometer (VSM). The developed technique of nano-composite synthesis is energy efficient since the reactions carried out in single step. The present catalyst is possible to be used for the production of biodiesel.

ChemInform Abstract: Rapid One‐Pot Aspartic Acid‐Promoted Synthesis of Tetrahydrobenzo[b]pyrans in Water.

AbstractThe title compounds are prepared by multicomponent reaction of dimedone, aryl aldehydes, and malononitrile using (.+‐.)‐aspartic acid as catalyst.

Efficient One-Pot Synthesis of Tetrahydrobenzo[b]pyrans by Ethylenediamine Diacetate-Catalyzed Multicomponent Reaction Under Solvent-Free Conditions

ABSTRACTEthylenediamine diacetate is found to be an efficient catalyst for the multicomponent condensation reaction of dimedone, aldehydes, and malononitrile to afford the corresponding tetrahydrobenzo[b]pyrans in good yields. The remarkable features of this new procedure are high yields, short reaction times, simple experimental and work-up procedures, mild and environmentally friendly reaction conditions, and economic availability of the catalyst.

ChemInform Abstract: Sulfonic Acid—Functionalized Magnetic Fe3‐xTixO4 Nanoparticles: New Recyclable Heterogeneous Catalyst for One‐Pot Synthesis of Tetrahydrobenzo[b]pyrans and Dihydropyrano[2,3‐c]pyrazole Derivatives.

AbstractSulfonic acid—functionalized magnetic Fe3‐xTixO4 nanoparticles are used as magnetic acidic catalyst for the one‐pot three‐component synthesis of (IV) and (VII).

Mechanistic Studies on the Three Component Synthesis of Tetrahydrobenzo[ b]pyran Catalyzed by Agar

Mechanistic Studies on the Three Component Synthesis of Tetrahydrobenzo[ b]pyran Catalyzed by Agar