Tris(hydroxymethyl)aminomethane as an efficient organobase catalyst for the synthesis of β-phosphonomalonates

被引:13
作者
Kalla, Reddi Mohan Naidu [1 ]
Kim, Il [1 ]
机构
[1] Pusan Natl Univ, Dept Polymer Sci & Engn, PLUS Ctr Adv Chem Technol BK21, Busan 609735, South Korea
关键词
beta-Phosphonomalonates; Organobase catalysis; Tris(hydroxymethyl)aminomethane; Solvent-free method; ONE-POT SYNTHESIS; PHOSPHA-MICHAEL ADDITION; STATE ANALOG INHIBITORS; SOLID ACID CATALYST; HIGHLY EFFICIENT; SOLVENT-FREE; 2-AMINO-4H-CHROMEN-4-YL PHOSPHONATES; ANTICANCER PROPERTIES; RECYCLABLE CATALYST; REUSABLE CATALYST;
D O I
10.1016/j.tetlet.2016.12.035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tris(hydroxymethyl)aminomethane (THAM) is a highly efficient and recyclable organobase catalyst for the nucleophilic phosphonylation of benzylidene malononitrile under solvent-free conditions. This new catalytic methodology is applicable without a solvent, eco-friendly, economically viable, avoids conventional isolation procedures, and has a facile work-up procedure and wide scope. THAM is an inexpensive, commercially available, non-toxic, and biodegradable novel organocatalyst. Furthermore, it can be reused in up to five cycles without loss in catalytic activity, and no chromatographic separation is needed to obtain the desired products. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:410 / 414
页数:5
相关论文
共 50 条
  • [1] Synthesis of Pyrano[2,3-d]pyrimidines Using tris(Hydroxymethyl)aminomethane as a Biodegradable and Reusable Organobase Catalyst
    Mohamadpour, Farzaneh
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2024, 56 (01) : 78 - 82
  • [2] Tris(hydroxymethyl)aminomethane (THAM): A recyclable and biodegradable organobase catalyst for green synthesis of 2-amino-4H-chromenes in an aqueous ethanol media
    Mohamadpour, Farzaneh
    RESULTS IN CHEMISTRY, 2024, 9
  • [3] A biocompatible synthesis of gold nanoparticles by Tris(hydroxymethyl)aminomethane
    Chen, Feng
    Wang, Yanwei
    Ma, Jun
    Yang, Guangcan
    NANOSCALE RESEARCH LETTERS, 2014, 9
  • [4] A biocompatible synthesis of gold nanoparticles by Tris(hydroxymethyl)aminomethane
    Feng Chen
    Yanwei Wang
    Jun Ma
    Guangcan Yang
    Nanoscale Research Letters, 9
  • [5] Thermophysical property characterization of tris(hydroxymethyl)aminomethane
    Soriano, Allan N.
    Cabahug, Denise Irene V.
    Li, Meng-Hui
    JOURNAL OF CHEMICAL THERMODYNAMICS, 2011, 43 (02) : 186 - 189
  • [6] Tris(hydroxymethyl)aminomethane Substitution into Octacalcium Phosphate
    Sugiura, Yuki
    Makita, Yoji
    CHEMISTRY LETTERS, 2019, 48 (11) : 1304 - 1307
  • [7] Synthesis and structural characterizations of tris (hydroxymethyl) aminomethane complexes with group IIA metals
    Albedair, Lamia A.
    KUWAIT JOURNAL OF SCIENCE, 2022, 49 (03)
  • [8] Synthesis, structure and properties of tris(hydroxymethyl)aminomethane complexes with biogenic metal salts
    Kondratenko, Y. A.
    Nikonorova, A. A.
    Zolotarev, A. A.
    Arsent'ev, M. Y.
    Nyanikova, G. G.
    Ugolkov, V. L.
    Sysoev, E. I.
    Kochina, T. A.
    INORGANICA CHIMICA ACTA, 2022, 530
  • [9] Efficient, Solvent-Free, Multicomponent Method for Organic-Base-Catalyzed Synthesis of β-Phosphonomalonates
    Kalla, Reddi Mohan Naidu
    Park, Huiju
    Lee, Hye Ri
    Suh, Hongsuk
    Kim, Il
    ACS COMBINATORIAL SCIENCE, 2015, 17 (11) : 691 - 697
  • [10] OXIDATION OF TRIS(HYDROXYMETHYL) AMINOMETHANE BY YEAST ALCOHOL-DEHYDROGENASE
    CHEN, DH
    HUANG, TC
    JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 1994, 27 (04) : 547 - 550