An amino acid@isopolyoxometalate nanoparticles catalyst containing aspartic acid and octamolybdate for the synthesis of functionalized spirochromenes

被引:31
作者
Heravi, Majid Momahed [1 ]
Momeni, Tayebeh [1 ]
Mirzaei, Masoud [2 ]
Zadsirjan, Vahideh [1 ]
Tahmasebi, Morteza [2 ]
机构
[1] Alzahra Univ, Sch Sci, Dept Chem, POB 1993891176, Tehran, Iran
[2] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, Mashhad, Razavi Khorasan, Iran
基金
美国国家科学基金会;
关键词
Octamolybdate; aspartic acid; amino acid; one-pot reaction; spirochromenes; heterogeneous catalyst; ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; EFFICIENT METHOD; MESOPOROUS SILICA; GREEN OXIDATION; DERIVATIVES; SPIROOXINDOLES; ALCOHOLS; HETEROCYCLES; NANOCATALYST;
D O I
10.1080/24701556.2020.1813172
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Amino acid polyoxometalate nanoparticles-embedded microcapsules were in situ fabricated by layer-by-layer (LbL) self-assembly method [isopolyoxometalate, Mo8O26 center dot nH(2)O; amino acid, aspartic acid (AFO)]. Aspartate functionalized gamma-octamolybdate (AFO) [Co-2(C4H6NO4)(2)(Mo8O26)(H2O)(10)]center dot 4H(2)Owas employed as heterogeneous catalyst for efficient, diverse, and high yielding synthesis of spirochromenesviaa three-component reaction involving isatins or acenaphthenequinone, malononitrile or ethyl cyanoacetate, and various 1,3-diketones (dimedone, barbituric acid, or ethyl acetoacetate) or 4-hydroxycoumarin/3-methyl-1H-pyrazol-5(4H)-one in water/ethanol under reflux. The AFO is characterized by some physico-chemical approaches such as elemental analysis, ICP, IR, and UV-Vis spectroscopies and PXRD analyses. Notably, the heterogeneous catalyst AFO, containing molybdenum atom as the basis and appropriate redox nature, reinforced with the organic metal fragment in its structure, showed effective catalytic activity, and could be recovered simply from the reaction mixture and reused at least three runs without significant loss of its catalytic activity. This prolific combination of amino acids and isopolyoxometalates inaugurates a powerful class of porous catalysts for the different chemical transformations, which overcomes key limitations of previously established salts and Lewis acidic metals based catalysts under low catalyst loading, the use of water scavengers, dry solvents, and additives for facilitating the specialized experimental setups commonly employed to the organic reactions.
引用
收藏
页码:896 / 909
页数:14
相关论文
共 80 条
  • [21] Harborne J.B., 2013, The Flavonoids: Advances in Research
  • [22] Silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a highly efficient, heterogeneous and recyclable silica-supported ionic liquid catalyst for the synthesis of benzo[b]pyran, bis(benzo[b]pyran) and spiro-pyran derivatives
    Hasaninejad, Alireza
    Golzar, Nooshin
    Beyrati, Maryam
    Zare, Abdolkarim
    Doroodmand, Mohammad Mahdi
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2013, 372 : 137 - 150
  • [23] The synthesis of coumarin-3-carboxylic acids and 3-acetyl-coumarin derivatives using heteropolyacids as heterogeneous and recyclable catalysts
    Heravi, Majid M.
    Sadjadi, Sainaheh
    Oskoole, Hossein A.
    Shoar, Rahim Hekmat
    Bamoharram, Fatemeh F.
    [J]. CATALYSIS COMMUNICATIONS, 2008, 9 (03) : 470 - 474
  • [24] Nitration of aromatic compounds catalyzed by divanadium-substituted molybdophosphoric acid, H5[PMo10V2O40]
    Heravi, Majid M.
    Bakhtiari, Khadijeh
    Benmorad, Tina
    Bamoharram, Fatemeh F.
    Oskooie, Hossein A.
    Tehrani, Maryam H.
    [J]. MONATSHEFTE FUR CHEMIE, 2007, 138 (05): : 449 - 452
  • [25] An efficient and chemoselective synthesis of acylals from aromatic aldehydes and their regeneration, catalyzed by 12-molybdophosphoric acid
    Heravi, Majid M.
    Bakhtiari, Khadijeh
    Bamoharram, Fatemeh F.
    [J]. CATALYSIS COMMUNICATIONS, 2006, 7 (07) : 499 - 501
  • [26] H14[NaP5W30O110]:: A heteropoly acid catalyzed acetylation of alcohols and phenols in acetic anhydride
    Heravi, Majid M.
    Behbahani, Farahnaz K.
    Bamoharram, Faterneh F.
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) : 16 - 19
  • [27] SYNTHESIS OF A NEW CLASS OF PHOSPHONATE DERIVATIVES USING A THREE COMPONENT REACTION OF TRIALKYL PHOSPHITES OR TRIARYL PHOSPHITES IN WATER
    Hossaini, Zinatossadat
    Rostami-Charati, Faramarz
    Ghambarian, Mehdi
    Siadati, Seyyed Amir
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (07) : 1177 - 1182
  • [28] Four-Component Reaction of Trialkyl Phosphites, Amines, and Electron-Deficient Acetylenic Compounds: Synthesis of Phosphonate Derivatives in Water
    Hossaini, Zinatossadat
    Rostami-Charati, Faramarz
    Ghasemian, Mahboubeh
    Abad, Saeid Afshari Sharif
    [J]. SYNLETT, 2015, 26 (09) : 1222 - 1224
  • [29] ZnO nanoparticles as a highly efficient heterogeneous catalyst for the synthesis of various chromene and pyrano[4,3-b]pyran derivatives under solvent-free conditions
    Hossaini, Zinatossadat
    Sheikholeslami-Farahani, Fatemeh
    Soltani, Samira
    Sayyed-Alangi, S. Zahra
    Sajjadi-Ghotabadi, Hadi
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (01) : 26 - 30
  • [30] 2 NEW BROMINATED TYROSINE DERIVATIVES FROM THE SPONGE DRUINELLA (=PSAMMAPLYSILLA) PURPUREA
    JAMES, DM
    KUNZE, HB
    FAULKNER, DJ
    [J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04): : 1137 - 1140