Fe3O4@Propylsilane@Histidine[HSO4‐] magnetic nanocatalysts: Synthesis,characterization and catalytic application for highly efficient synthesis of xanthene derivatives

The surface of Fe₃O₄ magnetic nanoparticles (MNPs) was modified by chloropropylsilane and histidine. The imidazole group of prepared Fe₃O₄@Propylsilane@Histidine MNPs converted to imidazolium hydrogen sulfate group and Fe₃O₄@Propylsilane@Histidine [HSO₄^‐] as a novel environmentally friendly ionic liquid/ magnetite nanoparticle was prepared, successfully. FT‐IR, XRD, SEM and TEM instruments was used to identifiy the histidine ionic liquids/magnetite nanoparticles (HILMNPs). The catalytic activity of synthesized HILMNPs was appraised for the synthesis of 9‐aryl‐1,8‐dioxooctahydroxanthene and spiro[indoline‐3,9′‐xanthene]trione derivatives. The activity of HILMNPs was much better than the other reported heterogeneous and homogeneous catalysts. Furthermore, the prepared catalyst could be separated from the reaction mixture and reused four times without any significant loss in its activity.     

Synthesis of some benzo[h]quinoline derivatives

Reaction between 6-methoxy-1-tetralone, methyl propiolate and an ammonia-saturated methanolic solution led to 5,6-dihydro-8-methoxybenzo[h]quinolin-2(1H)-one in good yields. Subsequent aromatization, chlorination, substitution and demethylation enabled us to prepare 2-amino-substituted benzo[h]quinoline derivatives. These compounds, which are structurally related to the antitumor benzo[c]phenanthridine alkaloids by deletion of a ring, were tested on cultured murine lymphoblastic leukaemia cells (L1210). Results showed that they are devoid of cytotoxicity.     

Application of [Fe3O4@SiO2@(CH2)3Py]HSO4− as heterogeneous and recyclable nanocatalyst for synthesis of polyhydroquinoline derivatives

Four‐component condensation reaction of aromatic aldehydes, dimedone, ethyl acetoacetate and ammonium acetate in the presence of a catalytic amount of ionic liquid on silica‐coated Fe₃O₄ nanoparticles as a heterogeneous, recyclable and very efficient catalyst provided the corresponding polyhydroquinoline derivatives in good to excellent yields in ethanol under reflux condition. The [Fe₃O₄@SiO₂@(CH₂)₃Py]HSO₄^? catalyst was characterized using various techniques such as scanning electron microscopy, powder X‐ray diffraction, thermogravimetric analysis, vibrating sample magnetometry and Fourier transform infrared spectroscopy. Furthermore, the recovery and reuse of the catalyst were demonstrated seven times without detectable loss in activity.     

Fe3O4@MCM-48-SO3H:An efficient magnetically separable nanocatalyst for the synthesis of benzo[f]chromeno[2,3-d]pyrimidinones

Sulfonic acid groups were grafted onto three different types of synthesized magnetic nanoparticles, namely Fe3O4, Fe3O4@SiO2, and Fe3O4@MCM‐48. The sulfonic acid‐functionalized nanoparticles were evalu...     

Fe3O4@MCM-48–SO3H:合成苯并[f]色烯并[2,3-d]嘧啶酮的高效、可磁性分离纳米催化剂（英文）

Sulfonic acid groups were grafted onto three different types of synthesized magnetic nanoparticles, namely Fe3O4, Fe3O4@SiO2, and Fe3O4@MCM‐48. The sulfonic acid‐functionalized nanoparticles were evaluated as catalysts for the synthesis of 5‐aryl‐1H‐benzo[f]chromeno[2,3‐d]pyrimidine‐2,4(3H,5H)‐dione derivatives in terms of activity and recyclability. Their catalytic activities were compared with that of the homogeneous acid catalyst 1‐methylimidazolium hydrogen sulfate ([HMIm][HSO4]). The activity of Fe3O4@MCM‐48–SO3H was comparable to those of the other heter‐ogeneous and homogeneous catalysts.     

Fe3O4@SiO2/collagen: An efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives

In this project, Fe₃O₄@SiO₂ was synthesized and combined with collagen for the preparation of Fe₃O₄@SiO₂/collagen. It was characterized by FT-IR, ¹H NMR, VSM, XRD, EDX, SEM and TEM. This nanocatalyst has some interesting advantages such as facile synthetic procedure, high catalytic activity, easy separation and acceptable reusability. It was applied as an efficient nanocatalyst in the synthesis of benzimidazole and benzothiazole derivatives. This method offers several advantages including high yields, short reaction times, easy workup process and environmentally benign reaction conditions.     

Synthesis of benzo[c][1,7]naphthyridine derivatives

Chemistry of Heterocyclic Compounds - Reactivity of 2-methyl-6-phenylbenzo[c][1,7]naphthyridine in alkylation, oxidation, and electrophilic substitution reactions has been studied. The reaction of...     

Synthesis and characterization of a novel functionalized magnetic Fe3O4 as a nanocatalyst for synthesis and antibacterial activities of 2-amino-3-phenylsulfonyl-4-aryl-4H-benzo[h]chromens derivatives and theoretical study on the mechanism using a DFT Method

Research on Chemical Intermediates - In this work, a new organic–inorganic hybrid heterogeneous and efficient magnetic nanocatalyst was fabricated with 4-aminopyridine (AP)-functionalized...     

Magnetic nanoparticles Fe3O4-supported guanidine as an efficient nanocatalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions

Research on Chemical Intermediates - Here, the application of guanidine supported on magnetic nanoparticles Fe3O4 (MNPs-guanidine) as a novel magnetically separable base nanocatalyst is described....     

Synthesis of 6-fluoroalkylbenzo[h]cyclopenta[c]quinoline and -benzo[c]phenanthridine derivatives

Russian Chemical Bulletin -     

Synthesis and characterization of Fe3O4@THAM-SO3H as a highly reusable nanocatalyst and its application for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives

In this work, a new, green and beneficial nanomagnetic catalyst was easily fabricated using sulfuric acid as an acidic group on Fe₃O₄ nanoparticles coated with tris (hydroxymethyl) aminomethane (THAM). The synthesized catalyst was characterized by FT-IR, TGA/DTG, XRD, TEM, EDS, VSM, and SEM analyses. Next, its catalytic activity was studied for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives. This catalyst has advantages such as high catalytic activity, non-toxicity, easy separation from the reaction mixture using an external magnet and reuses for several times without significantly reducing in its catalytic activity.     

Fe3O4-supported N-pyridin-4-amine-grafted graphene oxide as efficient and magnetically separable novel nanocatalyst for green synthesis of 4H-chromenes and dihydropyrano[2,3-c]pyrazole derivatives in water

Research on Chemical Intermediates - Fe3O4-magnetized N-pyridin-4-amine-functionalized graphene oxide [Fe3O4@GO-N-(pyridin-4-amine)] was readily prepared via a three-step procedure. The synthesized...     

Synthesis of benzo[c]selenophene and derivatives via new routes

[reaction: see text] Benzo[c]selenophene has been generated via facile bromination-dehydrobromination as well as oxidation of the 1,3-dihydrobenzo[c]selenophene. Benzo[c]selenophene thus generated has been lithiated in situ and treated with ClCOOEt to give the first functionalized derivative subject to X-ray crystallographic analysis.     

Synthesis of 4-oxo-3,4,5,6-tetrahydrospiro(benzo[h]quinazoline-5,1-cyclohexane) derivatives

The reaction of4-acylamino-3-cyano-1,2-dihydrospiro(naphthalene-2,1-cyclohexanes) with hydrogen chloride yields 2-substituted 4-oxo-3,4,5,6-tetrahydrospiro(benzo[h]quinazoline-5,1-cyclohexanes). It was found that when the latter are condensed with methyl iodide, N-alkylation takes place exclusively. Alkylation with ethyl iodide in analogous conditions yields a mixture of O- and N-substituted products.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 658–661, May, 1992.     

Synthesis of novel thiazolo[3,2-a]chromeno[4,3-d]pyrimidine-6(7H)-ones by bioactive Fe3O4@gly@thiophen@Cu(NO3)2 as reusable magnetic nanocatalyst

In this study, new Fe₃O₄@gly@thiophen@Cu(NO₃)₂ magnetic nanoparticles were synthesized. The final product was used as an efficient and novel magnetic nanocatalyst for synthesizing new derivatives of thiazolo[3,2-a] chromeno[4,3-d]pyrimidine-6(7H) in a short time and with higher efficiency. In the synthesis of Fe₃O₄@gly@thiophen@Cu(NO₃)₂ magnetic nanoparticles, the use of glycine proved an inexpensive and readily available coating for Fe₃O₄ than previously reported materials, and the structure was confirmed using scanning electron microscopy, transmission electron microscopy, X-ray diffraction, energy-dispersive x-ray (EDX) spectroscopy, EDX mapping, Fourier-transform infrared spectroscopy, thermogravimetric analysis/derivative thermogravimetry, and vibrating sample magnetometry. The biological properties of magnetic nanoparticles were evaluated, and they exhibited acceptable antifungal and antibacterial properties in terms of minimum inhibitory concentration, minimum fungicidal concentration, and minimum bactericidal concentration.     

Green synthesis of pyrido[2,1-a]isoquinolines and pyrido[1,2-a]quinolins using Fe3O4-MNPs as efficient nanocatalyst: Study of antioxidant activity

In this work, synthesis of pyrido[2,1-a]isoquinolines and pyrido[1,2-a]quinolins in excellent yield using multicomponent reaction of phthalaldehyde, methyl amine, methyl malonyl chloride, alkyl bromides, and triphenylphosphine in the presence of catalytic amount of Fe₃O₄-MNPs with aqueous sodium hydroxide at 80°C was investigated. The reduction of ferric chloride solution with Clover Leaf water extract caused to synthesis of magnetic iron oxide nanoparticles (Fe₃O₄-MNPs) as a green method. As well, antioxidant activity was studied for the some newly synthesized compounds such as 6a , 6c , 9b , and 9c using the DPPH radical trapping and reducing of ferric ion experiments and comparing results with synthetic antioxidants (TBHQ and BHT). As a result, compounds 6a , 6c , 9b , and 9c show good DPPH radical trapping and excellent reducing strength of ferric ion.     

Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe3O4@PS‐arginine as an efficient chiral magnetic nanocatalyst

A novel chiral magnetic nanocatalyst was prepared by the surface modification of Fe₃O₄ magnetic nanoparticles (MNPs) with a chloropropylsilane and further by arginine to form Fe₃O₄@propylsilan‐arginine (Fe₃O₄@PS‐Arg). After the structural confirmation of Fe₃O₄@PS‐Arg synthesized MNPs by Fourier transform‐infrared, X‐ray diffraction, field emission‐scanning electron microscopy, transmission electron microscopy, vibrating‐sample magnetometry and thermogravimetric analyses, their catalytic activity was evaluated for one‐pot enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives. The results showed that in the presence of 0.07 g Fe₃O₄@PS‐Arg nanocatalyst and ethanol as solvent, the best reaction yield (96%) was obtained in the least time (5 min). Easy operation, reusability and stability, short reaction time, high reaction yields and good enantioselectivity are the major advantages of the newly synthesized nanocatalyst. Also, this study provides a novel strategy for further research and investigation on the synthesis of new reusable enantioselective catalysts and chiral compounds.     

Sulfonic acid-functionalized Fe3O4-supported magnetized graphene oxide quantum dots: A novel organic-inorganic nanocomposite as an efficient and recyclable nanocatalyst for the synthesis of dihydropyrano[2,3-c]pyrazole and 4H-chromene derivatives

In this research, the main emphasis has been focused on the preparation of a novel Fe₃O₄-supported propane-1-sulfonic acid-grafted graphene oxide quantum dots (Fe₃O₄@GOQD-O-(propane-1-sulfonic acid)) that it was readily synthesized via a five-step procedure as a hitherto unreported magnetic nanocatalyst. This newly prepared Fe₃O₄@GOQD-O-(propane-1-sulfonic acid) nanocomposite was structurally well-established by different analytical techniques including Fourier transform infrared (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray (EDX), thermal gravimetric analysis (TGA), field emission gun-scanning electron microscope (FESEM), high-resolution transmission electron microscopy (HRTEM) and vibrating sample magnetometer (VSM) analyses. The high catalytic performance of this nanocomposite was exhibited in one-pot synthesis of dihydropyrano[2,3-c]pyrazole and 4H-chromene derivatives under mild conditions. Low reaction times, excellent yields of the products, benignity of the catalyst, easy reaction work-up and magnetic recyclability of the catalyst are the main advantages of the present protocol. Also, our research indicated that the Fe₃O₄@GOQD-O-(propane-1-sulfonic acid) could be reused up to five times without considerable loss of catalytic activity.     

Fe3O4@SiO2/Schiff base complex of metal ions as an efficient and recyclable nanocatalyst for the green synthesis of quinoxaline derivatives

Fe₃O₄@SiO₂/Schiff base complex of metal ions catalyzed the reaction between phenylene-1,2-diamines and 1,2-diketones to produce quinoxalines in aqueous media at room temperature. This eco-friendly method provides several advantages such as mild reaction conditions, good to excellent yields, simple work-up, and nanocatalyst stability. Also, nanocatalyst can be simply recovered by a magnetic field and reused for at least five successive reactions.     

Behavior of 5,6-dihydrobenzo[h]cinnolinones towards hydrazine. Synthesis of benzo[h]cinnolinones and of 4-Aminobenzo[h]cinnolinones

Dehydrogenation and amination of 4,4a,5,6-tetrahydro and 5,6-dihydrobenzocinnolinones in refluxing hydrazine hydrate to give new benzo[h]cinnolinones and 4-aminobenzo[h]cinnolinones are reported, and reaction mechanisms proposed. Experiments were also extended to 4,4a-dihydro-5H-indenopyridazinone which underwent hydrazine induced dehydrogenation to 5H-indenopyridazin-3-one but not subsequent amination.