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
  • [41] SYNTHESIS AND PROPERTIES OF 2-SUBSTITUTED OR 2,5-SUBSTITUTED THIOPHENE AND 2-SUBSTITUTED OR 2,5'-SUBSTITUTED DITHIOPHENE DERIVATIVES OF PLATINUM
    KOTANI, S
    SHIINA, K
    SONOGASHIRA, K
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 429 (03) : 403 - 413
  • [42] Enantioselective synthesis of tertiary alcohols by the desynnnetrizing benzoylation of 2-substituted glycerols
    Jung, Byunghyuck
    Hong, Mi Sook
    Kang, Sung Ho
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) : 2616 - 2618
  • [43] REACTION OF 2-SUBSTITUTED BENZOTHIAZOLES WITH DICHLOROCARBENE
    RAO, JS
    IYENGAR, DS
    RAO, SN
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1990, 29 (03): : 280 - 281
  • [44] SYNTHESIS AND REACTION OF 1-SUBSTITUTED AND 2-SUBSTITUTED TETRAZOLE-5-ALDEHYDES
    MODERHAC.D
    ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESSELSCHAFT, 1972, 305 (01): : 71 - &
  • [45] 2-SUBSTITUTED METHYLENECYCLOPROPANES IN THE REACTION WITH DIHALOCARBENES
    AKHACHINSKAYA, TV
    DONSKAYA, NA
    KALYAKINA, IV
    OPRUNENKO, YF
    SHABAROV, YS
    ZHURNAL ORGANICHESKOI KHIMII, 1989, 25 (08): : 1645 - 1651
  • [46] Reaction of tetracyanoethylene with 2-substituted cyclohexanones
    Sheverdov, VP
    Ershov, OV
    Nasakin, OE
    Chernushkin, AN
    Tafeenko, VA
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (07) : 1001 - 1004
  • [47] Reaction of Tetracyanoethylene with 2-Substituted Cyclohexanones
    V. P. Sheverdov
    O. V. Ershov
    O. E. Nasakin
    A. N. Chernushkin
    V. A. Tafeenko
    Russian Journal of Organic Chemistry, 2002, 38 : 1001 - 1004
  • [48] SYNTHESIS OF 2-SUBSTITUTED AND 2,5-SUBSTITUTED BENZOXAZOLES AND BENZOTHIAZOLES
    SOLOSKI, EJ
    MOORE, GJ
    TAMBORSKI, C
    JOURNAL OF FLUORINE CHEMISTRY, 1976, 8 (04) : 295 - 304
  • [49] A new 'one-pot' synthesis of 2-substituted 3-nitropyrrolidines through a multicomponent domino reaction
    Baricordi, N
    Benetti, S
    Biondini, G
    De Risi, C
    Pollini, GP
    TETRAHEDRON LETTERS, 2004, 45 (07) : 1373 - 1375
  • [50] 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