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
  • [1] Synthesis of 2-substituted quinolines from alcohols
    Xu, Xuefeng
    Zhang, Xu
    Liu, Wenming
    Zhao, Qiang
    Wang, Zhiqiang
    Yu, Lintao
    Shi, Fu
    TETRAHEDRON LETTERS, 2015, 56 (24) : 3790 - 3792
  • [2] Fluorination of 2-substituted benzo[b]furans with Selectfluor™
    Wang, Mingliang
    Liu, Xixi
    Zhou, Lu
    Zhu, Jidong
    Sun, Xun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) : 3190 - 3193
  • [3] Synthesis of 2-substituted oxazoloquinazolinones
    Bobileva, Olga
    Loza, Einars
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (11) : 1070 - 1074
  • [4] The Synthesis of 2-substituted Benzo[b]furans Catalyzed by Ni/5-Bromo-2,2'-bipyridine
    Rong, Zhou
    Yu-qin, Li
    Yan-li, Ding
    Xiao-li, Qin
    Jing, Sha
    Ping, Li
    Lu, Jin
    Huan-huan, Wang
    LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (12) : 1149 - 1153
  • [5] Pd/C mediated synthesis of 2-substituted benzo[b]furans/nitrobenzo[b]furans in water
    Pal, M
    Subramanian, V
    Yeleswarapu, KR
    TETRAHEDRON LETTERS, 2003, 44 (45) : 8221 - 8225
  • [6] Facile synthesis of 2-substituted benzofurans by intermolecular [3+2] cycloaddition of benzoquinone and vinyl azides under air
    Sun, Pengfei
    Yu, Xin
    Wei, Fang
    TETRAHEDRON, 2024, 167
  • [7] Copper-catalyzed domino reaction between 1-(2-halophenyl) methanamines and amidines or imidates for the synthesis of 2-substituted quinazolines
    Omar, Mohamed A.
    Conrad, Juergen
    Beifuss, Uwe
    TETRAHEDRON, 2014, 70 (18) : 3061 - 3072
  • [8] Synthesis of 2-Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence
    Koudelka, Jakub
    Tobrman, Tomas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (22) : 3260 - 3269
  • [9] Simple Synthesis of Some 2-Substituted Melatonin Derivatives
    Lozinskaya, Natalia A.
    Sosonyuk, Sergey E.
    Volkova, Maria S.
    Seliverstov, Michael Yu.
    Proskurnina, Marina V.
    Bachurin, Sergey E.
    Zefirov, Nikolay S.
    SYNTHESIS-STUTTGART, 2011, (02): : 273 - 276
  • [10] Synthesis of 2-Substituted Furans by Iron-and Palladium-Catalyzed Coupling Reactions
    Haner, Jamie
    Jack, Kelsey
    Nagireddy, Jaipal
    Raheem, Mohammed Abdul
    Durham, Robin
    Tam, William
    SYNTHESIS-STUTTGART, 2011, (05): : 731 - 738
12345