Recyclization of 3-formylchromone with phenacyl thiocyanate: fast and efficient access to thiophenes and 2-aminothiophenes bearing o-acylphenol moiety

被引:9
作者
Alizadeh, Abdolali [1 ]
Rezaiyehraad, Reza [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran
关键词
O-Acylphenol skeleton; 3-formylchromone; phenacyl thiocyanate; thiophene; 2-aminothiophene; FRIES REARRANGEMENT; ONE-POT; BOND; DERIVATIVES; FUNCTIONALIZATION; SCAFFOLD; DESIGN;
D O I
10.1080/17415993.2021.2007920
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A variety of substituted derivatives of thiophene and 2-aminothiophene bearing o-acylphenol moieties were obtained via the reaction between 3-formylchromone with phenacyl thiocyanate in the presence of Et3N. This metal-free procedure for the synthesis of thiophene skeletons revealed a good efficiency, higher diversity, and wide substrate tolerance. These compounds have structural similarities to biologically active compounds reported in the literature. Besides, they can be used as a suitable candidate for the synthesis of fused-thiophene heterocycles through C-H activation processes.
引用
收藏
页码:264 / 274
页数:11
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共 44 条
  • [1] Bioconversion of silybin to phase I and II microbial metabolites with retained antioxidant activity
    Abourashed, Ehab A.
    Mikell, Julie R.
    Khan, Ikhlas A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (09) : 2784 - 2788
  • [2] Synthesis of 1H-Thiopyrano[4,3-c]quinoline Scaffold via One-pot Three-component Cyclization
    Alizadeh, Abdolali
    Rezaiyehraad, Reza
    Roosta, Atefeh
    Halvagar, Mohammad Reza
    [J]. CHEMISTRYSELECT, 2019, 4 (41): : 12049 - 12052
  • [3] Triethylammonium thiolate as an efficient reagent for synthesis of quinoxaline containing indandione substitution via sequential one-pot multicomponent reaction
    Alizadeh, Abdolali
    Ghasemzadeh, Hossein
    Rezaiyehraad, Reza
    Xiao, Hong-Ping
    [J]. JOURNAL OF SULFUR CHEMISTRY, 2019, 40 (06) : 614 - 628
  • [4] Ultrasonic Methylation of Triethylammonium Thiolate as a Key Strategy for Synthesis of Tetrahydropyrazine-Containing 2-Oxindole Scaffold
    Alizadeh, Abdolali
    Rezaiyehraad, Reza
    Halvagar, Mohammadreza
    [J]. CHEMISTRYSELECT, 2019, 4 (01): : 130 - 133
  • [5] Efficient one pot and chemoselective synthesis of functionalized 3-bromo-4,5-dihydroisoxazole derivatives &ITvia &IT1,3-dipolar cycloaddition reactions of nitrile oxides
    Alizadeh, Abdolali
    Roosta, Atefeh
    Rezaiyehrad, Reza
    Halvagar, Mohammadreza
    [J]. TETRAHEDRON, 2017, 73 (48) : 6706 - 6711
  • [6] Efficient synthesis of chromenopyridines containing intramolecular hydrogen bonds through a sequential three-component reaction
    Alizadeh, Abdolali
    Bayat, Fahimeh
    Zhu, Zhe
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (06) : 5927 - 5936
  • [7] Highly Regioselective Synthesis of Pyrazole Derivatives Using a 1,3-Dipolar Cycloaddition Approach
    Alizadeh, Abdolali
    Moafi, Leila
    Zhu, Long-Guan
    [J]. SYNLETT, 2016, 27 (04) : 595 - 598
  • [8] Highly mild approach towards synthesis of tetrasubstituted thiophenes by an organic salt afforded by cyclic thioureas and ketene dithioacetals
    Alizadeh, Abdolali
    Vahabi, Amir Hossein
    Bazgir, Ayoob
    Khavasi, Hamid Reza
    Zhu, Zhe
    Ng, Seik Weng
    [J]. RSC ADVANCES, 2015, 5 (103): : 85028 - 85034
  • [9] The solar-chemical photo-Friedel-Crafts heteroacylation of 1,4-quinones
    Benites, Julio
    Rios, David
    Diaz, Pilar
    Valderrama, Jaime A.
    [J]. TETRAHEDRON LETTERS, 2011, 52 (05) : 609 - 611
  • [10] Simple and quick preparation of α-thiocyanate ketones in hydroalcoholic media. Access to 5-aryl-2-imino-1,3-oxathiolanes
    Bisogno, Fabricio R.
    Cuetos, Anibal
    Lavandera, Ivan
    Gotor, Vicente
    [J]. GREEN CHEMISTRY, 2009, 11 (04) : 452 - 454