A FACILE SYNTHESIS OF 2-ACETYLNAPHTHO[2,3-B]FURAN-4,9-DIONE

被引：16
|
作者：
KOYANAGI, J
YAMAMOTO, K
NAKAYAMA, K
TANAKA, A
机构：
[1] Faculty of Pharmaceutical Science, Josai University, Saitama, 350-02, 1-1 Keyakidai, Sakado-shi
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1995年 / 32卷 / 04期
关键词：
D O I：
10.1002/jhet.5570320432
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of the parent naphtho[2,3-b]furan-4,9-dione 2 with various electrophilic reagents was difficult, and only nitration of 2 gave small amounts of 2-nitronaphtho[2,3-b]furan-4,9-dione 4. Then 2-acetylnaphtho[2,3-b]furan-4,9-dione 1 was not obtained by the acetylation of 2. On the other hand, compound 1 that is isolated from Tabebuia Cassinoides and has cytotoxic activity, was obtained from 3-lithiofuran in five steps.
引用
收藏
页码：1289 / 1291
页数：3
相关论文
共 50 条
  • [1] A SHORT-STEP SYNTHESIS OF NAPHTHO[2,3-B]FURAN-4,9-DIONE
    KOYANAGI, J
    YAMAMOTO, K
    NAKAYAMA, K
    TANAKA, A
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (05) : 1303 - 1304
  • [2] Nucleophilic substitutions of 2-halonaphtho[2,3-b]furan-4,9-diones and 2-nitronaphtho[2,3-b]furan-4,9-dione
    Koyanagi, J
    Yamamoto, K
    Nakayama, K
    Tanaka, A
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1997, 45 (10) : 1579 - 1581
  • [3] Nucleophilic substitutions of 2-chloronaphtho[2,3-b]furan-4,9-dione with amines
    Koyanagi, J
    Ogawa, M
    Yamamoto, K
    Nakayama, K
    Tanaka, A
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (02) : 301 - 305
  • [4] EFFICIENT REGIOSPECIFIC SYNTHESIS OF 2 CYTOTOXIC FURONAPHTHOQUINONES, 5,7-DIMETHOXY-4,9-DIHYDRONAPHTHO[2,3-B]FURAN-4,9-DIONE AND 5,6,7-TRIMETHOXY-4,9-DIHYDRONAPHTHO[2,3-B]FURAN-4,9-DIONE
    PERRY, PJ
    PAVLIDIS, VH
    HADFIELD, JA
    COUTTS, IGC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (09): : 1085 - 1087
  • [5] A new synthetic route to 2-substituted naphtho[2,3-b]furan-4,9-dione
    Koyanagi, J
    Yamamoto, K
    Nakayama, K
    Tanaka, A
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (02) : 407 - 412
  • [6] Short-step synthesis of 1,3-disubstituted naphtho[2,3-c]furan-4,9-dione and naphtho[2,3-b]furan-4,9-dione by the Friedel-Crafts reaction
    Koyama, J
    Toyokuni, I
    Kino, A
    Tagahara, K
    [J]. HETEROCYCLES, 1998, 48 (08) : 1631 - 1638
  • [7] Naphtho[2,3-b]furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
    Li, Jimei
    Zhang, Jie
    Li, Mingfei
    Zhang, Chenyang
    Yuan, Yongkun
    Liu, Renhua
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (16) : 2348 - 2351
  • [8] SYNTHESIS OF 2-ACETYL-4H,9H-NAFTA-[2,3-B]FURAN-4,9-DIONE(1)E (+/-) 2-(1-HYDROXYMETHYL)-4H,9H-NAFTO[2,3-B]FURAN-4,9-DIONE (2)
    LOPES, CC
    LOPES, RSC
    COSTA, PRR
    PINTO, AV
    [J]. ANAIS DA ACADEMIA BRASILEIRA DE CIENCIAS, 1983, 55 (03): : 317 - 317
  • [9] STRUCTURE OF 8-HYDROXY-2-(1-HYDROXYETHYL)NAPHTHO[2,3-B]FURAN-4,9-DIONE
    KOGO, H
    SAKAI, Y
    OHASHI, Y
    FUJIMOTO, Y
    IKEKAWA, T
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1991, 47 : 1127 - 1129
  • [10] The synthesis of 5-hydroxy-3-methylnaphtho[2,3-c]furan-4,9-dione and 5,8-dihydroxy-1-methylnaphtho[2,3-c]furan-4,9-dione
    Piggott, MJ
    Wege, D
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (07) : 691 - 702
12345