Bronsted acid promoted one-pot synthesis of 4-aryl-3,4-dihydrocoumarins

被引：5
作者：
Chen, Cheng [2 ]
Zhang, Rui [1 ]
Lin, Long [1 ]
Yang, Guang-Fu [1 ]
Wu, Qiong-You [1 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
[2] Wuhan Univ Technol, State Key Lab Adv Technol Mat Synth & Proc, Wuhan 430070, Peoples R China
来源：
TETRAHEDRON | 2016年 / 72卷 / 27-28期
基金：
中国国家自然科学基金;
关键词：
Dihydrocoumarins; Friedel-Crafts alkylation; Cycloaddition; Bronsted acid; Perchloric acid; MEDIATED HYDROARYLATION; MICROWAVE IRRADIATION; BENZYLIC ALCOHOLS; DIHYDROCOUMARINS; PHENOLS; COUMARINS; EFFICIENT; TANNINS; ARENES; DERIVATIVES;
D O I：
10.1016/j.tet.2016.05.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4-Aryl-3,4-dihydrocoumarins are a class of valuable molecules demonstrating attractive pharmaceutical and biological properties. In this paper, we designed a new and facile approach to synthesis of 4-aryl-3,4-dihydrocoumarin derivatives by Bronsted acid catalyzed Friedel Crafts alkylation and cycloaddition reaction. With this protocol, 15 examples of 4-aryl-3,4-dihydrocoumarins were successfully prepared with yields ranging from 82 to 99%. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3917 / 3921
页数：5
相关论文
共 43 条
  • [1] A convenient synthesis of dihydrocoumarins from phenols and cinnamic acid derivatives
    Aoki, S
    Amamoto, C
    Oyamada, J
    Kitamura, T
    [J]. TETRAHEDRON, 2005, 61 (39) : 9291 - 9297
  • [2] Solvent-free Bronsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols
    Barbero, Margherita
    Cadamuro, Silvano
    Dughera, Stefano
    Rucci, Marta
    Spano, Giulia
    Venturello, Paolo
    [J]. TETRAHEDRON, 2014, 70 (09) : 1818 - 1826
  • [3] Unprecedented reactivity pattern of chromium Fischer carbene complexes. Direct application to one-pot synthesis of 4-aryl-3,4-dihydrocoumarins on a multigram scale
    Barluenga, Jose
    Andina, Facundo
    Aznar, Fernando
    [J]. ORGANIC LETTERS, 2006, 8 (13) : 2703 - 2706
  • [4] Synthesis of neoflavonoids: 4-(4'-methoxyphenyl)3,4-dihydrocoumarins
    Bezerra, MZB
    Machado, MIL
    deMorais, SM
    Braz Filho, R
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 1997, 8 (03) : 229 - 234
  • [5] SYNTHESIS OF 3-HYDROXY-3-CYCLOHEXYLBUTYRIC ACID-DERIVATIVES .2. CYCLIC ANALOGS OF MEVALONIC ACID
    CARGANICO, G
    COZZI, P
    ORSINI, G
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (12) : 1767 - 1769
  • [6] Lewis Acid-Catalyzed Diastereoselective Hydroarylation of Benzylidene Malonic Esters
    Duan, Shaofeng
    Jana, Ranjan
    Tunge, Jon A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) : 4612 - 4614
  • [7] Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
    Escobar, Angelica M.
    Ruiz, Diego M.
    Autino, Juan C.
    Romanelli, Gustavo P.
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (12) : 10109 - 10123
  • [8] Yb(OTf)3-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols:: One-pot assembly of 3,4-dihydrocoumarins, 4-chromanones, coumarins, and chromones
    Fillion, E
    Dumas, AM
    Kuropatwa, BA
    Malhotra, NR
    Sitler, TC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) : 409 - 412
  • [9] Direct oxidative cyclization of 3-arylpropionic acids using PIFA or Oxone: synthesis of 3,4-dihydrocoumarins
    Gu, Yonghong
    Xue, Kun
    [J]. TETRAHEDRON LETTERS, 2010, 51 (01) : 192 - 196
  • [10] HSU FL, 1985, CHEM PHARM BULL, V33, P3142
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