A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans

被引:10
|
作者
Makarov, Anton S. [1 ]
Kekhvaeva, Anna E. [1 ]
Chalikidi, Petrakis N. [2 ]
Abaev, Vladimir T. [2 ]
Trushkov, Igor, V [3 ,4 ]
Uchuskin, Maxim G. [1 ]
机构
[1] Perm State Univ, Bukireva St 15, Perm 614990, Russia
[2] KL Khetagurov North Ossetian State Univ, Vatutina St 46, Vladikavkaz 362025, Russia
[3] Dmitry Rogachev Natl Res Ctr Pediat Hematol Oncol, Samory Mashela St 1, Moscow 117997, Russia
[4] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Pr 47, Moscow 119991, Russia
来源
SYNTHESIS-STUTTGART | 2019年 / 51卷 / 19期
基金
俄罗斯科学基金会;
关键词
furan; benzofuran; rearrangement; sugikurojinol B; ONE-POT SYNTHESIS; POLYSUBSTITUTED FURANS; OXIDATIVE CYCLIZATION; INHIBITOR; PALLADIUM; ALKYNYLPHENOLS; DERIVATIVES; DISCOVERY; REUPTAKE; INDOLES;
D O I
10.1055/s-0039-1690000
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Bro''nsted acid-catalyzed cascade synthesis of densely substituted benzofurans from easily available salicyl alcohols and biomass-derived furans has been developed. The disclosed sequence includes the intermediate formation of 2-(2-hydroxybenzyl)furans that quickly rearrange into functionalized benzofurans. The established protocol was applied for the total synthesis of sugikurojinol B.
引用
收藏
页码:3747 / 3757
页数:11
相关论文
共 50 条
  • [21] SIMPLE, MILD, AND HIGHLY EFFICIENT SYNTHESIS OF 2-SUBSTITUTED BENZIMIDAZOLES AND BIS-BENZIMIDAZOLES
    Eren, Bilge
    Bekdemir, Yunus
    QUIMICA NOVA, 2014, 37 (04): : 643 - 647
  • [22] Simple and Efficient One-Pot Synthesis of 2-Substituted Benzoxazole and Benzothiazole
    Patil, Sachin S.
    Bobade, Vivek D.
    SYNTHETIC COMMUNICATIONS, 2010, 40 (02) : 206 - 212
  • [23] Recent Advances in the Synthesis of 2-Substituted Oxetanes
    Davis, Owen A.
    Bull, James A.
    SYNLETT, 2015, 26 (10) : 1283 - 1288
  • [24] Asymmetric synthesis of 2-substituted cyclic amines
    Kudale, Amit A.
    Anaspure, Prasad
    Goswami, Falguni
    Voss, Matthew
    TETRAHEDRON LETTERS, 2014, 55 (52) : 7219 - 7221
  • [25] Synthesis and antibacterial activity of 2-substituted benzothiazoles
    Stremski, Y.
    Statkova-Abeghe, S.
    Georgiev, D.
    Angelov, P.
    Ivanov, I.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2017, 49 : 32 - 36
  • [26] Progress in Synthesis of 2-Substituted Benzothiazole Compounds
    Zhang, Jun
    Liu, Yafei
    Zhang, Yurong
    Hu, Liang
    Han, Shiqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (03) : 1053 - 1071
  • [27] Synthesis of several new 2-substituted benzimidazoles
    Han, Xiao-Feng
    Chen, Man-Man
    Zhou, Zhi-Mimg
    JOURNAL OF CHEMICAL RESEARCH, 2015, (07) : 407 - 409
  • [28] Progress in the Synthesis of 2-Substituted Benzoxazoles Derivatives
    Xiao, Liwei
    Gao, Hongjie
    Kong, Jie
    Liu, Guangxian
    Peng, Xiaoxia
    Wang, Shujun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (06) : 1048 - 1060
  • [29] Synthesis and antiplatelet activity of 2-substituted imidazolines
    Sultanova, R. M.
    Khusnutdinova, N. S.
    Borisova, Yu. G.
    Raskildina, G. Z.
    Meshcheryakova, S. A.
    Samorodov, A. V.
    Zlotskii, S. S.
    RUSSIAN CHEMICAL BULLETIN, 2023, 72 (07) : 1711 - 1716
  • [30] Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles
    Bahrami, Kiumars
    Khodaei, Mohammad M.
    Nejati, Akbar
    GREEN CHEMISTRY, 2010, 12 (07) : 1237 - 1241