Straightforward synthesis of quinoxaline-furan bis-heterocyclic structures via a multicomponent reaction

被引:0
|
作者
Farhid, Hassan [1 ]
Araghi, Hanieh Mohammadi [1 ]
Shaabani, Ahmad [1 ]
Notash, Behrouz [2 ]
机构
[1] Shahid Beheshti Univ, Dept Organ Chem, GC, POB 19396-4716, Tehran, Iran
[2] Shahid Beheshti Univ, Dept Inorgan Chem & Catalysis, Tehran 1983969411, Iran
关键词
Higher-order multicomponent reactions; Bis-heterocycles; Isocyanide; Furan; Quinoxaline; DIMETHYL ACETYLENEDICARBOXYLATE; 4-COMPONENT REACTION; ONE-POT; DERIVATIVES; INHIBITORS; ISOCYANIDES; STRATEGY; DESIGN;
D O I
10.1016/j.molstruc.2023.136143
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient and straightforward synthetic strategy based on the higher-order multicomponent reactions (MCRs) is established for the synthesis of quinoxaline-furan bis-heterocyclic structures. The process includes a one-pot, pseudo-five component reaction of 3,4-diaminobenzoic acid, a 1,2-dicarbonyl compound, a dialkyl acetylenedicarboxylate, and two equivalents of an isocyanide as the readily available precursors. The noticeable features of the method are pot and atom economy, seven new bond formations, operational simplicity, high yields, and applicability on the gram-scale. Indolo[2,3-b]quinoxaline-furan tris-heterocycles were also synthesized using isatin derivatives via consecutive reactions.
引用
收藏
页数:8
相关论文
共 50 条
  • [1] Synthesis of oxazepin-quinoxaline bis-heterocyclic scaffolds via an efficient three component synthetic protocol
    Hajishaabanha, Fatemeh
    Shaabani, Ahmad
    RSC ADVANCES, 2014, 4 (87) : 46844 - 46850
  • [2] New bis-heterocyclic structures: Synthesis, characterization and biological activity
    Farhan, Marwan Mohammed
    Al-Jumaili, Mohammed Hadi Ali
    Bakr, Ekhlas Aziz
    JOURNAL OF CHEMICAL RESEARCH, 2023, 47 (06)
  • [3] (Z)-Stereoselective Synthesis of Mono- and Bis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction
    Xu, Zhigang
    Martinez-Ariza, Guillermo
    Cappelli, Alexandra P.
    Roberts, Sue A.
    Hulme, Christopher
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18): : 9007 - 9015
  • [4] Synthesis and antimicrobial activity of bis-heterocyclic sulfamoyl acetamides
    Divya, K.
    Sravya, G.
    Padmaja, A.
    Padmavathi, V.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (07) : 4413 - 4426
  • [5] Synthesis and antimicrobial activity of bis-heterocyclic sulfamoyl acetamides
    K. Divya
    G. Sravya
    A. Padmaja
    V. Padmavathi
    Research on Chemical Intermediates, 2015, 41 : 4413 - 4426
  • [6] Parallel Synthesis of Bis-heterocyclic Isoxazolylmethyl- and Isoxazolinylmethylpyrazoles
    Meng, Liping
    Lorsbach, Beth A.
    Sparks, Thomas C.
    Fettinger, James C.
    Kurth, Mark J.
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01): : 129 - 136
  • [7] Bis-thiourea Derivatives and Their Utility in Synthesis of Mono-heterocyclic, Bis-heterocyclic, and Fused Heterocyclic Systems
    Dawood, Kamal M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (06) : 1701 - 1721
  • [8] Synthesis and tautomeric structures of some novel thiophene-based bis-heterocyclic monoazo dyes
    Karci, Fikret
    Karci, Fati
    JOURNAL OF MOLECULAR STRUCTURE, 2012, 1024 : 117 - 122
  • [9] Synthesis and biological activities of novel bis-heterocyclic pyrrodiazole derivatives
    He, Feng-Qi
    Liu, Xing-Hai
    Wang, Bao-Lei
    Li, Zheng-Ming
    HETEROATOM CHEMISTRY, 2008, 19 (01) : 21 - 27
  • [10] Synthesis and Analysis of Some Bis-Heterocyclic Compounds Containing Sulphur
    Mabkhot, Yahia Nasser
    MOLECULES, 2009, 14 (05): : 1904 - 1914