• Title/Summary/Keyword: One-pot three component synthesis

Search Result 32, Processing Time 0.018 seconds

Synthesis of Imidazo[1,2-a]pyridines and Pyrido[1,2-a]pyrimidines in Water and their SNAr Cyclizations

  • Chanu, Langpoklakpam Gellina;Singh, Thokchom Prasanta;Jang, Yong Ju;Yoon, Yong-Jin;Singh, Okram Mukherjee;Lee, Sang-Gyeong
    • Bulletin of the Korean Chemical Society
    • /
    • v.35 no.4
    • /
    • pp.994-1000
    • /
    • 2014
  • Synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydropyrido[1,2-a] pyrimidines by a one-pot and three component reaction of ${\alpha}$-oxoketenedithioacetals, diamines and DMAD in water has been described. Different routes for accessing the desired compounds were examined and a few specially designed-substrates have been utilized further to afford the new imidazo and pyrido fused [1,8] naphthyridine tetracyclic compound by $S_NAr$ intramolecular cyclization.

Efficient One-Pot Three-Component Synthesis of Monomethine Cyanine Dyes with Quinoline Nucleus and Their Spectral Properties

  • Fu, Y.L.;Zhang, B.R.;Wang, S.;Gao, X.X.;Wang, L.Y.
    • Bulletin of the Korean Chemical Society
    • /
    • v.34 no.2
    • /
    • pp.489-494
    • /
    • 2013
  • An improved method for the preparation of monomethine cyanine dyes with quinoline nucleus by one-pot three-component using 1-methyl-2-quinolinethione, quaternized 2- or 4-methylheterocyclic compounds and methyl p-toluenesulfonate as starting materials was described. Compared with the traditional methods, the new synthetic method reduced the reaction steps, shortened the reaction time, avoided the separation and purification of the intermediate and reduced cost. The dyes absorbed in the region 478.0-563.0 nm and had molar extinction coefficients of $1.3{\times}10^4-9.4 {\times}10^4L\;mol^{-1}\;cm^{-1}$. Their fluorescence maxima and Stokes shifts were in the range of 525.2-594.4 nm and 16.2-80.6 nm in different solvents, respectively. From the spectral properties of the dyes in different solvents, it could be found that the ${\lambda}_{max}$ of the dyes were shorter in protonic solvents, and showed hypsochromic shifts with the increase of polarity of the solvents.

Three Component Solvent-free Synthesis of Chroman-2,4-dione-based Heterocyclic Ketene Aminal (HKA) Derivatives by "GAP" Chemistry

  • Yu, Fu-Chao;Hao, Xiao-Pan;Jiang, Xiu-Yang;Yan, Sheng-Jiao;Lin, Jun
    • Bulletin of the Korean Chemical Society
    • /
    • v.35 no.6
    • /
    • pp.1625-1632
    • /
    • 2014
  • A concise and efficient one-pot synthesis of chroman-2,4-dione-based HKA derivatives by three component reaction of HKAs, triethoxymethane and 4-hydroxycoumarin derivatives under solvent-free and catalyst-free conditions is described. This protocol has many advantages, in that the GAP (Group-Assistant-Purification) chemistry process is involved in this method. As a result, the experimenter can avoid cumbersome process steps such as traditional chromatography and recrystallization purifications. The desired products can be easily obtained by washing the crude products with 95% EtOH.

Highly Selective Synthesis of β-Amino Carbonyl Compounds over ZSM-5-SO3H under Solvent-free Conditions

  • Massah, Ahmad Reza;Kalbasi, Roozbeh Javad;Samah, Neda
    • Bulletin of the Korean Chemical Society
    • /
    • v.32 no.5
    • /
    • pp.1703-1708
    • /
    • 2011
  • ZSM-5-$SO_3H$ efficiently catalyzed the one-pot three-component Mannich reaction of aldehydes, anilines, and ketones. ${\beta}$-Aminocarbonyl compounds were obtained in reasonable yields and excellent stereoselectivities when the reaction was carried out at room temperature under solvent-free conditions. Simple experimental conditions and product isolation procedure makes this protocol potential for the development of clean and environment-friendly strategy for the synthesis of ${\beta}$-amino-ketones. The catalyst was recovered and reused for subsequent runs.

An Efficient Synthesis of 2,4,5-Triaryl-1H-Imidazole Derivatives Catalyzed by Boric Acid in Aqueous Media Under Ultrasound-Irradiation

  • Shelke, Kiran F.;Sapkal, Suryakant;Sonal, Swapnil;Madje, Balaji R.;Shingate, Bapurao B.;Shingare, Murlidhar S.
    • Bulletin of the Korean Chemical Society
    • /
    • v.30 no.5
    • /
    • pp.1057-1060
    • /
    • 2009
  • Boric acid ($BO_3H_3$) is an inexpensive, efficient and mild catalyst for the synthesis of 2,4,5-triaryl-1H-imidazoles in excellent yields from the one-pot three-component condensation of benzil/benzoin, an aldehydes and ammonium acetate in aqueous media under ultrasound at room temperature. The remarkable advantages offered by this method are green catalyst, mild reaction conditions, simple procedures, much faster reactions and excellent yield of products.

Very Efficient and Rapid Catalyst-free One-pot Three Component Synthesis of 2,5-Dihydro-5-imino-2-methylfuran-3,4-dicarboxylate Derivatives Under Ultrasound Irradiation

  • Rouhani, Morteza;Ramazani, Ali;Joo, Sang Woo;Hanifehpour, Younes
    • Bulletin of the Korean Chemical Society
    • /
    • v.33 no.12
    • /
    • pp.4127-4130
    • /
    • 2012
  • We report a fast, efficient, and facile route for the synthesis of 2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylate derivatives from the isocyanide, dialkyl acetylenedicarboxylate and acetic anhydride under ultrasound-assisted conditions. Utilization of easy reaction conditions, very high to excellent yields, and short reaction times makes this manipulation potentially very useful.

Polymer Support Immobilized Acidic Ionic Liquid: Preparation and Its Application as Catalyst in the Synthesis of Hantzsch 1,4-Dihydropyridines

  • Jahanbin, Bentolhoda;Davoodnia, Abolghasem;Behmadi, Hossein;Tavakoli-Hoseini, Niloofar
    • Bulletin of the Korean Chemical Society
    • /
    • v.33 no.7
    • /
    • pp.2140-2144
    • /
    • 2012
  • A polymer support immobilized acidic ionic liquid was prepared by copolymerization of 3-vinyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate with styrene in the presence of benzoyl peroxide and its primary application as a solid acidic heterogeneous catalyst to the synthesis of Hantzsch 1,4-dihydropyridines through a one-pot three-component reaction of aromatic aldehydes, ethyl acetoacetate and ammonium acetate was investigated. The results showed that this heterogeneous catalyst has high catalytic activity and the desired products were obtained in good to high yields. Moreover, the catalyst was found to be reusable and a considerable catalytic activity still could be achieved after third run.

Magnetic Nanoparticle Immobilized N-Propylsulfamic Acid as a Recyclable and Efficient Nanocatalyst for the Synthesis of 2H-indazolo[2,1-b]phthalazine-triones in Solvent-Free Conditions: Comparison with Sulfamic Acid

  • Rostami, Amin;Tahmasbi, Bahman;Yari, Ako
    • Bulletin of the Korean Chemical Society
    • /
    • v.34 no.5
    • /
    • pp.1521-1524
    • /
    • 2013
  • N-Propylsulfamic acid supported onto magnetic $Fe_3O_4$ nanoparticles (MNPs-PSA) was used as an efficient and magnetically recoverable catalyst for synthesis of 2H-Indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives from the three-component, one-pot condensation reaction of phthalhydrazide, aromatic aldehydes and cyclic 1,3-diones, in good to excellent yields at $100^{\circ}C$ under solvent-free conditions. The catalyst was easily separated with the assistance of an external magnetic field from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency. In order to compare, the synthesis of 2H-Indazolo[ 2,1-b]phthalazine-1,6,11(13H)-trione derivatives in the presence of catalytic amount of sulfamic acid (SA) under same reaction condition was also reported.

One-pot, Three-component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanoimino)triphenylphosphorane, Aromatic Carboxylic acids and (1R)-(-)-Campherchinon

  • Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Abdian, Behnaz;Rouhani, Morteza
    • Bulletin of the Korean Chemical Society
    • /
    • v.33 no.2
    • /
    • pp.453-458
    • /
    • 2012
  • Reactions of (N-isocyanimino)triphenylphosphorane with (1R)-(-)-campherchinon in the presence of aromatic carboxylic acids proceed smoothly at room temperature and in neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed.

Montmorillonite Clay Catalyzed Three Component, One-Pot Synthesis of 5-Hydroxyindole Derivatives

  • Reddy, B.V. Subba;Reddy, P. Sivaramakrishna;Reddy, Y. Jayasudhan;Bhaskar, N.;Reddy, B. Chandra Obula
    • Bulletin of the Korean Chemical Society
    • /
    • v.34 no.10
    • /
    • pp.2968-2972
    • /
    • 2013
  • A highly efficient and environmentally benign protocol has been developed for the first time to produce a wide range of biologically active 5-hydroxyindole derivatives using montmorillonite KSF clay as a reusable solid acid catalyst. The use of recyclable clay makes this procedure quite simple, more convenient and cost-effective.