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  • Open access
  • 153 Reads
Basic GO-Imidazolium ionic liquid as a recoverable nanocatalyst for the synthesis of pyrrole derivatives

Ionic liquid with basic properties is a significant category in the wide-ranging ionic liquid field. Ionic liquids are mostly made of ions and ion pairs. They are known as powerful solvents which have potential applications. Since the 1999 review by Welton which is about room temperature ionic liquids, ionic liquids have grown as a motivating research area in the last 15 years. Some ionic liquids are liquid at room temperature include some nitrogen-based compounds. Among them, imidazolium-based ionic liquids are the most important ones. In imidazole-based ionic liquids, their physical properties like melting point and acidity-basicity could be adjusted by changing the alkyl substituents and ion pairs. Most of room temperature ionic liquids involve bulky organic cations such as 1-alkyl-3-methylimidazolium, 1-alkylpyridinium and ammonium ion. To have heterogeneous nanocatalysts using ionic liquids, it was studied that carbonaceous substrates with high surface area like graphene oxide could be the best choice.

To this purpose and to have heterogeneous basic nanocatalyst with high surface area and significant catalytic activity, basic GO-Imidazolium ionic liquid was synthesized in this research. Here, N-methyl imidazole was used as cation, HCO3- as anion and GO as solid support to form basic ionic liquid nanocatalyst and its catalytic ability was used in synthesis of pyrroles as a significant N-heterocycle compound with important biological and pharmacological activity.

  • Open access
  • 170 Reads
Oxidative bromination reaction using NBS and magnetic IBX

Halogenated and brominated compounds are important groups of chemicals and have varied applications in several fields. Cross-coupling reactions in organic chemistry can be performed via aromatic functionalization process with halide aromatic compounds. Therefore, in coupling reactions like Heck, Suzuki, Sonogashira and hetero coupling reactions, halide compounds are the key fragments.

Br2 is the old reagent for the formation of brominated compounds. Using Br2 caused to produce HBr as a corrosive chemical, need accurate control of temperature and control of amount of Br2. So, established better brominating agents have been developed in recent years. To this purpose, NBS was used for brominating reactions and several conditions in organic reactions have been reported to activate the halogenating ability of NBS.

2-iodoxybenzoic acid, IBX, has gained massive interest as an efficient and useful oxidant which can be used for the oxidation of alcohols. in addition of this, magnetic form of catalysts have more advantages compare to normal form of them due to their simply work-up procedures. So, to gain better nanocatalyst with the advantages of magnetic catalysts, we used a simple method to prepare magnetized IBX. To develop efficient catalysts for oxidation reaction, we report the catalytic application of a magnetized IBX as an efficient and recoverable catalyst in the presence of NBS for oxidation reaction.

  • Open access
  • 136 Reads
Synthesis and biological properties of alkyl diaryl disulfides derivatives

Diaryl disulfides compounds are valuable intermediates as they have multifaceted applications in pharmaceutical industry as well as in the field of material science. They are used as novel stabilizer for the tumor suppressor Pdcd4 [1] and by virtue of the reversibility of disulfide bond, plays an integral role in the synthesis of bioactive compounds. Numerous examples of drugs use for diabetes, Alzheimer’s and Parkinson’s diseases, inflammatory and immune diseases have aryl sulfide moieties in their structures [2].  Lipophilicity is also known to influence the biological activity of various compounds [3]. Increasing the lipophilic character of the diaryl disulfide system enhances the anti-bacterial properties [4,5]. Therefore, in continuation of our efforts in the synthesis of biologically active organo sulfur compounds, we herein report the synthesis of disulfanediyldibenzamides of enhanced lipophilic character by introducing long alkyl chain C8-C12 at amino end in order to deliver electrophilic sulphur species more effectively into the bacterial cell wall. These dialkyl diaryl disulphides compounds were characterised by spectral and analytical data. They were also found to have interesting anti-bacterial properties over a panel of gram positive and gram negative bacteria.

  • Open access
  • 199 Reads
1,3,5-Tris (2-hydroxyethyl) isocyanurate-Cu II functionalized magnetic graphene oxide (MGO-THEIC-CuII): a highly efficient and recoverable nanocatalyst for the one-pot synthesis of substituted benzimidazoles under microwave irradiation

Benzimidazole and its derivatives are considered as a significant class of heterocycle compounds because of their abundance in naturally occurring molecules and broad medicinal applications.[1] They possess special activities such as anticancer, antiglycation, antiprotozoal, anti-inflammatory, anti-urease, anti-HIV, anti-fungals, anti-bacterial, proton pump inhibitors, anti-viral, anti-oxidant, anti-viral and analgesic.[2],[3],[4]

In the last decade, several methods have been proposed for synthesis of highly substituted benzimidazole derivatives. However, majority of the reported procedures for the synthesis of benzimidazoles have some limitations in terms of the use of excess amounts of catalysts, formation of byproducts and unsatisfactory yields, lengthy reaction times, difficult work-up and significant amounts of waste materials.[5] Therefore, development of new methodologies and introducing recoverable catalysts to overcome aforementioned disadvantages is still desirable.

In continuation of our ongoing efforts to develop efficient catalysts for different MCRs,[6] we report herein the catalytic application of 1,3,5-Tris (2-hydroxyethyl) isocyanurate-Cu(II) functionalized magnetic graphene (MGO-THEIC-CuII) as a new, highly efficient and recoverable catalyst, for the synthesis of benzimidazoles derivatives under microwave irradiation.[7]

[1] Hanoon, H.D.; Kowsari, E.; Abdouss, M. et al. Res Chem Intermed 2017, 43: 1751.

[2] Narasimhan, B.; Sharma, D.; Kumar, P. Medicinal Chemistry Research 2012, 21:269–283.

[3] Swami, M.B.; Jadhav, A.H.; Mathpati, S.R. et al. Res Chem Intermed 2017, 43: 2033.

[4] Bui, H. T. B.; Ha, Q. T. K.; Oh, W. K. et al. Tetrahedron letters 2016, 57(8), 887-891.

[5] Dekamin, M. G.; Arefi, E.; Yaghoubi, A. RSC Advances 2016, 6(90), 86982-86988.

[6] Dekamin, M. G.; Eslami, M. Green Chemistry 2014, 16, 4914.

[7] Dekamin, M. G.; Mehdipoor, F.; Yaghoubi, A. New Journal of Chemistry 2017, 00, 1‐10.

  • Open access
  • 106 Reads
Nickel ferrite nanoparticle as a magnetic catalyst: Synthesis and dye degradation

The aim of this work is the synthesis of NiFe2O4 and Co-doped NiFe2O4 nanoparticles to catalyze photodegradation of direct red 264 under visible light. So, NiFe2O4 and Co-doped NiFe2O4 nanoparticles were synthesized by a sol-gel auto-combustion method. The catalysts were characterized by X-ray diffraction (XRD), scanning electron microscope (SEM), Fourier transform infrared (FT-IR) and diffuse reflectance spectra (DRS).

In recent years, the waterways polluted with azo dyes cause serious environmental problems, so they must be removed. Direct Red 264 (DR264) was used as a model. The effects of NiFe2O4 and Co-doped NiFe2O4 nanoparticles as catalysts were studied on photocatalytic degradation of DR 264 in typical wastewater using visible light irradiation. UV-vis spectrophotometer was used to measure concentration of dyes before and after degradation.

The effects of doping on dye degradation were investigated. The results shows doping did not remarkable effect on photocatalytic properties.

  • Open access
  • 124 Reads
Highly efficient synthesis of benzopyranopyrimidine derivatives catalyzed by functionalized superparamagnetic graphene oxide as a new and recoverable catalyst

In multicomponent reactions (MCRs), three or more reactants come together in a single reaction vessel to form new products that contain structural units of all the components. This type of reaction becomes progressively important in organic and medicinal chemistry because it allows obtaining highly sophisticated polyfunctional molecules through simple one-pot procedures. [1–3] Benzopyrano[2,3-d]pyrimidins (BPP’s) are vital pharmacophore that exhibits antitumor activity, cytotoxic activity against cancer cell lines and can cause significant perturbation in cell cycle kinetics. In continuation of our ongoing efforts towards to develop efficient catalysts for different MCRs[4] ,We report herein functionalized superparamagnetic graphene oxide as a new and heterogeneous catalyst for the synthesis of benzopyranopyrimidine derivatives in high yields via a one-pot, pseudo four-component condensation of salicylaldehydes, malononitrile and secondary amines under mild conditions at room temperature. [5-6] (Scheme 1). It should be noted that the significant advantages of this procedure are low catalyst loading, short reaction times, high to excellent yields, simple workup, reusability of the catalyst and simple purification of the products.

  • Open access
  • 90 Reads
Synthesis and Properties of Thienothiophene-Boron for OLED Application

Synthesis of conjugated organic molecules having electronic and optical properties suitable for electrochromic devices (ECD), organic light emitting diode (OLED), organic field effective transistors (OFET), lasers, photodiodes and solar cell applications have gained importance in recent years.1-3 Based on the previous studies on thienothiophenes (TT),2,3  new donor-acceptor materials,4-[5-[bis-(2,4,6-trimethyl-phenyl)-boranyl]-2-(4-diphenylamino-phenyl)-thieno[3,2-b]thiophen-3-yl]-benzonitrile containing π-conjugated system and having electron withdrawing cyano group and acceptor boron4 were designed and synthesized. Its electronic and optical properties were investigated. It has been found to be suitable for OLED applications.

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