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
相关论文
共 44 条
  • [41] Evaluation of the antiproliferative activity of 2-amino thiophene derivatives against human cancer cells lines
    Veras Of Aguiar, Andreza Conception
    Moura, Ricardo Olimpio Of
    Bezerra Mendonca Junior, Jaime Francisco
    de Oliveira Rocha, Hugo Alexandre
    Gomes Camara, Rafael Barros
    Carvalho Schiavona, Manuela dos Santos
    [J]. BIOMEDICINE & PHARMACOTHERAPY, 2016, 84 : 403 - 414
  • [42] Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids
    Wang, Dahai
    Cui, Sunliang
    [J]. TETRAHEDRON, 2015, 71 (45) : 8511 - 8516
  • [43] Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage
    Xie, Ying
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (83) : 12372 - 12375
  • [44] Zita P., 2009, Nova Biotech, V9, P167, DOI DOI 10.36547/NBC.1274