A straightforward synthesis of 1,2-dihydronaphtho[2,1-b]furans from 2-naphthols

被引：0
|
作者：
Arrault, A [1 ]
Touzeau, F [1 ]
Guillaumet, G [1 ]
Mérour, JY [1 ]
机构：
[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 2, France
来源：
SYNTHESIS-STUTTGART | 1999年 / 07期
关键词：
2-naphthols; ethyl 1,2-dihydronaphtho[2,1-b]furan-2-carboxylates; aromatization; 1,2-dihydronaphtho [2,1-b]furan-2-carbonitrile; 1-(1,2-dihydronaphtho[2,1-b]furan-2-yl)ethan-1-one;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-step synthesis of ethyl 1,2-dihydronaphtho[2,1-b]furan-2-carboxylates 2a-g from substituted 2-naphthols and ethyl 2,3-dibromopropanoate is described. 3,4-Dibromobutan-2-one and 2-chloroacrylonitrile react with 2-naphthol (1a) to afford the corresponding 2-cyano- or 2-acetylnaphtho[2,1-b]furans 6 and 7, respectively.
引用
收藏
页码：1241 / 1245
页数：5
相关论文
共 50 条
  • [1] Convenient synthesis of novel 2,2-dialkyl-1,2-dihydronaphtho[2,1-b]furans
    Vaughan, Doug
    Jha, Amitabh
    TETRAHEDRON LETTERS, 2009, 50 (41) : 5709 - 5712
  • [2] ONE-POT GREEN SYNTHESIS OF NOVEL POLYSUBSTITUTED 1,2-DIHYDRONAPHTHO[2,1-b]FURANS
    Sadeghpour, Mandieh
    Olyaei, Abolfazl
    Lotfiyan, Jamshid
    Rajabi, Fatemeh
    SYNTHETIC COMMUNICATIONS, 2015, 45 (11) : 1311 - 1320
  • [3] Approach to Construct Polysubstituted 1,2-Dihydronaphtho[2,1-b]furans and Their Aerobic Oxidative Aromatization
    Huo, Congde
    Xu, Xiaolan
    An, Jinzhu
    Jia, Xiaodong
    Wang, Xicun
    Wang, Cheng
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18): : 8310 - 8316
  • [4] Synthesis of Chiral 1,2-Dihydronaphtho[2,1-b]furans by Organocatalytic Domino Reactions Catalyzed with Multiple Catalysis
    Pan, Jin-Yun
    Li, Xin-Sheng
    Xu, Dong-Cheng
    Xie, Jian-Wu
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2013, 66 (11) : 1415 - 1421
  • [5] Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols
    Man, Ningning
    Li, Yuming
    Jie, Jiyang
    Li, Hongyun
    Yang, Haijun
    Zhao, Yufen
    Fu, Hua
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (50) : 12884 - 12889
  • [6] FACILE SYNTHESIS OF 1-AMINO-1,2-DIHYDRONAPHTHO[2,1-B]FURANS THROUGH REACTION OF SCHIFF-BASES WITH DIMETHYLOXOSULPHONIUM METHYLIDE
    NADIR, UK
    CHAURASIA, BP
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (03): : 189 - 190
  • [7] Reactions of o-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-b]furans and 2,3-Dihydrobenzofurans
    Osyanin, Vitaly A.
    Osipov, Dmitry V.
    Klimochkin, Yuri N.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5505 - 5520
  • [8] Oxidative rearrangement of 3-aryl-1H-benzo[f]chromenes into 2-aroyl-1,2-dihydronaphtho[2,1-b]furans
    Kirill S. Korzhenko
    Dmitry V. Osipov
    Vitaly А. Osyanin
    Maxim R. Demidov
    Yuri N. Klimochkin
    Chemistry of Heterocyclic Compounds, 2021, 57 : 599 - 601
  • [9] Oxidative rearrangement of 3-aryl-1H-benzo[f]chromenes into 2-aroyl-1,2-dihydronaphtho[2,1-b]furans
    Korzhenko, Kirill S.
    Osipov, Dmitry V.
    Osyanin, Vitaly A.
    Demidov, Maxim R.
    Klimochkin, Yuri N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (05) : 599 - 601
  • [10] HETEROCYCLES FROM YLIDES .6. CONVENIENT SYNTHESIS OF 2-ACYL-SUBSTITUTED OR 2-AROYL-SUBSTITUTED 2,3-DIHYDROBENZOFURANS AND 1,2-DIHYDRONAPHTHO[2,1-B]FURANS
    CADON, L
    CROCE, PD
    SYNTHESIS-STUTTGART, 1976, (12): : 800 - 801
12345