فهرست مطالب

Organic Chemistry Research
Volume:1 Issue: 1, Summer 2015

  • تاریخ انتشار: 1394/06/10
  • تعداد عناوین: 12
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  • Issa Yavari *, Manijeh Nematpour, Esmat Sodagar Pages 1-5

    The synthesis of a novel class of 2-oxoindolin-3-ylidene-(1-arylhydrazinyl)-2-aryl(alkyl)ethylidene derivativesvia a copper-catalyzed tandem reaction of isatin, arylhydrazines, sulfonyl azides and terminal alkynes is described.

    Keywords: 2-Oxoindolines, Ketenimines, Sulfonyl azide, Terminal alkyne, Isatin
  • Hossein Eshghi *, Mohammad Rahimizadeh, Nazanin Noroozi Shad, Hossein Sabet Sarvestania Pages 6-11

    A novel podand based anion receptor bearing benzimidazole motifs as recognition sites was designed and synthesized by reaction of 1,7-bis(2'-methylbenzoate)-1,4,7-trioxaheptane and phenylenediamine. The binding properties of anionic guest with this receptor were studied using UV-Vis and fluorescence spectroscopy. These studies revealed that this receptor exhibit selective recognition towards F- ionamong other anions such as HSO4-, ClO4-, Cl-, Br- and I- in methanol through intermolecular hydrogen bonding of guest and host. Also, we have focused our attention on the receptor-F- with theoretical computation based on DFT/B3LYP/6-31G(d).

    Keywords: Fluorescence, Receptor, UV-Vis spectroscopy, Fluoride, Podand
  • Ali Ramazani *, Morteza Rouhani, Sang Woo JOO Pages 12-17

    The synthesis of aryl amides via the reactions of carboxylic acids and isocyanides in methanol was carried out in 78-95% yields under ultrasound irradiation. The method has wide applicability, and the protocol is mild, fast and efficient compared to the existing methods based on silent conditions.

    Keywords: Ultrasound, Aryl amides, Carboxylic acid, Isocyanide
  • Saeed Balalaie *, Fatemeh Tahoori, Negin Khatibi Pages 18-26

    A simple and efficient one-pot, three-component Strecker reaction of protected amino acids, aromatic aldehydes, and trimethylsilyl cyanide has been developed for the synthesis of chiral α-amino nitriles. The reaction was carried out in the presence of catalytic amount of phosphotungstic acid (H3[P(W3O10)4]) as an environmentally friendly catalyst.

    Keywords: Strecker reaction, Protected α-amino acid, Heteropoly acid, Phosphotungstic acid, Trimethylsilyl cyanide, Environmentally friendly catalyst, Diastereoselectivity
  • Elahe Yazdani, Kobra Azizi, Athar Nakisa, Akbar Heydari* Pages 27-36

    We have reported the fabrication of boric acid incorporated into surface of magnetite nanoparticles. The catalyst was characterized using spectroscopic, magnetic and thermal techniques (FT-IR, SEM, XRD, ICP, VSM and TGA). It catalyzed Mukaiyama aldol reaction of a ketene silyl acetal type nucleophile ((1-methoxy-2-methylprop-1-enyloxy) trimethylsilane), and various aldehydes (aromatic, aliphatic, α,β-unsaturated), in acetonitrile and the yields were in the range of 45-98%. Magnetic Fe3O4-boric acid was multi-functional. The Fe3O4 core of the catalyst made easy separation and recycling while its boric acid portion catalyzed Mukaiyama aldol reaction. Nano size nature of the catalyst increased its activity in a way that boric acid, which is a weak Lewis acid, functioned similar to a more strong one like BF3. Boric acid functionality had the advantage of being moisture insensitive, economically reasonable and environmentally friendly. Furthermore Fe3O4@ SiO2@Boric acid was magnetically recovered via an external permanent magnet and was reused at least 6 times with a negligible change in its activity.

    Keywords: Mukaiyama, Boric acid, Magnetic catalyst
  • Kaveh Khosravi *, Mina Marashi Pages 37-44

    Gem-dihydroperoxides as nearly stable peroxidic derivatives of aldehydes and ketones are known important intermediates in synthesis of anti-malaria drugs. Also, because containing high concentration of peroxidic oxygen, recently, some of these compounds have been used as solid, efficient and powerful oxidants in many oxidation organic reactions. Generally, these compounds are synthesized via peroxidation of aldehydes and ketones. So, regarding the importance of gem-dihydroperoxides, in this work, boric acid has been explored as an effective, inexpensive, commercially available, green and homogenous solid catalyst for catalyze peroxidation of aldehydes and ketones to corresponding gem-dihydroperoxides by 30% aqueous hydrogen peroxide at room temperature in acetonitrile as the solvent. Both aromatic and aliphatic aldehydes and ketones were studied in this work. The reactions were carried on in short times. The products were obtained in high yields and good purity. In all reaction, no any by-product was observed. This methodology is easy, mild, nearly green, efficient and available.

    Keywords: Gem-dihydroperoxide, Aldehyde, Ketones, Boric acid, Hydrogen peroxide
  • Dariush Saberi *, Khodabakhsh Niknam, Farhad Panahi, MohammadReza Hormozi Nezhad Pages 45-52

    Silica-grafted n-propyl-diaza-15-crown-5 (SGPDC) with immobilized palladium nanoparticles was found as an efficient heterogeneous catalytic system for the Heck and Suzuki coupling reactions and satisfied results were obtained. Different derivatives of aryl halides and alkenes under the Heck reaction were converted to the corresponding products with good efficiency. The presence of electron-donating groups on the aryl moiety of aryl halide derivatives retarded the reaction and led to the drop of yields. In contrast, higher efficiency was observed when electron-withdrawing groups were accommodated on the aryl halide. As well as, a variety of bi-phenyl derivatives were well synthesized by the coupling reaction between aryl halides and aryl boronic acids derivatives via the Suzuki reaction. Reusability of the catalyst was examined in both Heck and Suzuki reactions under optimized conditions. The catalyst could be recycled several times without any treatment in its catalytic activity. The TEM image of the catalyst utilized in the Heck reaction after seven times of recyclability indicates that the morphology and size of the nanoparticles have remained almost intact.

    Keywords: Aza-crown ether, Heterogeneous catalysis, Palladium nanoparticle, Heck reaction, Suzuki reaction
  • Bi Bi Fatemeh Mirjalili *, Abdolhamid Bamoniri, MohammadAli Mirhoseini Pages 53-58

    Heterogeneous reagent systems have many advantages such as simple experimental procedures, mild reaction conditions and minimization of chemical wastes as compared to the liquid phase counterparts. Al(HSO4)3 as an heterogeneous, efficient, readily available, and cheap catalyst was synthesized and applied for the synthesis of 1,3-benzo[d]thiazole derivatives by condensation protocol of 2-aminothiophenol and aldehydes under solvent free conditions. Short reaction times, high yields, a clean process, simple methodology, easy work-up and green conditions are some advantages of this protocol.

    Keywords: 3-Benzo[d]thiazole, Benzothiazoles, Al(HSO4)3, Aluminium hydrogen sulfate
  • Mehdi Kalhor * Pages 59-65

    A one-pot multicomponent reaction of aryl aldehydes, 2-amino benzimidazole and ethyl 2-mercaptoacetate is described as an efficient and environmentally method for the synthesis of  some  novel  ethyl  2-((1H-benzo[d]imidazol-2-ylamino)(Aryl)methylthio)  acetates  in  the presence of nano-Copper Y Zeolite (NCZ) as a catalyst in ethanol at room temperature. After optimizing of reaction conditions for this reaction, the amount of catalyst obtained was 10W%. The yield of reactions was in the range of 75-89%. The synthesized compounds 4a-j were characterized using IR, 1H NMR, 13C NMR spectroscopy and Elemental Analysis.  The  present  procedure  offers  several advantages,  such  as  use  of  available,  safety  and reusable of  the  catalyst,  high  yields,  short reaction  times,  easy  and  quick  isolation  of  the  product. This  method  may  provide a developed groundwork  for  the  synthesis  of  new  commercial  fungicide  Benomyl  and  Carbendazim derivatives. Also, this procedure may be used as a synthetic pathway for preparation of new sulfur-bearing peptide derivatives based on 2-amino benzimidazole core under mild conditions.

    Keywords: One-pot reaction, 2-Amino benzimidazole, Aryl aldehyde, Catalyst, Transition nano metal Zeolite
  • Mir Rasul Mousavi *, Malek Taher Maghsoodlou, Fatemeh Noori, Nourallah Hazeri Pages 66-71

    A very efficient one-pot three-component synthesis of pyran derivatives has been improved by condensation of aldehydes and malononitrile with dimedone under 80 °C using sucrose as natural and biodegradable catalyst in water. This method offers some advantages including inexpensive, high to quantitative yields, short reaction time, and easy work-up. Therefore, this methodology is entirely green and environmentally benign protocol for the preparation of tetrahydrobenzo[b]pyran derivatives.

    Keywords: sucrose, Malononitrile, Multi-component reactions (MCRs), Tetrahydrobenzo[b]pyran
  • Alireza Kiasat *, Hossein Almasi, Seyyed Jafar Saghanezhad Pages 72-77

    Phosphosulfonic acid (PSA) was found to be an efficient catalyst for the one-pot three-component Hantzsch condensation reaction of arylaldehydes, ethylacetoacetate and ammonium acetate to afford the corresponding 1,4-dihydropyridine and polyhydroquinoline derivatives in high yields. PSA was also applied for the one-pot preparation of polyhydroquinolines via four-component reaction of arylaldehydes, ethylacetoacetates, dimedone and ammonium acetate. The main advantages of the present approach are short reaction times, clean reaction profiles, catalyst recyclability, and facile experimental and workup procedures.

    Keywords: 4-dihydropyridines, Polyhydroquinolines, Phosphosulfonic acid, Recyclable heterogeneous catalyst, Solvent-free conditions
  • Khodabakhsh Niknam *, Nassim Borazjani Pages 78-86

    Silica-bonded N-propyldiethylenetriamine sulfamic acid (SPDTSA) is employed as a recyclable heterogeneous solid acid catalyst for the synthesis of benzopyrano[2,3-d]pyrimidines  through one-pot condensation reaction of salicylaldehydes, malononitrile and secondary amines  at room temperature under solvent-free conditions. SPDTSA showed much the same efficiency when used in consecutive reaction runs.

    Keywords: Benzopyrano[2, 3-d]pyrimidines, Heterogeneous catalysts, Solid acids, Synthesis, Solvent-free conditions