Novel methods of synthesizing naphtho[1,2-c]furan-1,3-dione and benzo[e]isoindole-1,3-dione

被引:3
|
作者
Mizuno, M [1 ]
Yamano, M [1 ]
机构
[1] Takeda Pharmaceut Co Ltd, Div Pharmaceut Prod, Chem Dev Labs, Yodogawa Ku, Osaka 5328686, Japan
关键词
D O I
10.3987/COM-05-S(T)78
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Convenient methods of synthesizing naphtho[1,2-c]furan-1,3-dione and benzo[e]isoindole-1,3-dione from phenylbutyric acid derivatives have been established. Naphtho[1,2-c]furan-1,3-dione and benzo[e]isoindole-1,3-dione were obtained respectively from 4,5-dihydronaphtho[1,2-c]furan-1,3-dione and 4,5-dihydrobenzo[e]isoindole-1,3-dione by aromatization with 10% Pd-C in AcOH under mild conditions. In addition, benzo[e]isoindole-1,3-dione derivatives were obtained from 4,5-dihydronaphtho [ 1,2-c] furan-1,3 -dione by imidation and simultaneous aromatization with primary amine in AcOH in one pot.
引用
收藏
页码:807 / +
页数:9
相关论文
共 50 条
  • [31] New Isoindole-1,3-dione Substituted Sulfonamides as Potent Inhibitors of Carbonic Anhydrase and Acetylcholinesterase: Design, Synthesis, and Biological Evaluation
    Gundogdu, Saliha
    Turkes, Cuneyt
    Arslan, Mustafa
    Demir, Yeliz
    Beydemir, Sukru
    CHEMISTRYSELECT, 2019, 4 (45): : 13347 - 13355
  • [32] Exploring the Potential of Isoindole-1,3-Dione Derivatives as Novel Inhibitors of Aldose Reductase: An In Silico and In Vitro Insight into Therapeutic Strategies for Diabetic Complications
    Sengul, Buelent
    Gundogdu, Ozlem
    Kilinc, Namik
    Kishali, Nurhan
    CHEMISTRYSELECT, 2024, 9 (36):
  • [33] 1,3-Dipolar cycloaddition of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones and nitrile oxides: An experimental and theoretical investigation
    Efremova, Mariia M.
    Molchanov, Alexander P.
    Novikov, Alexander S.
    Starova, Galina L.
    Muryleva, Anna A.
    Slita, Alexander, V
    Zarubaev, Vladimir V.
    TETRAHEDRON, 2020, 76 (15)
  • [34] Synthesis and optical properties of some isoindole-1,3-dione compounds: Optical band gap, refractive index and absorbance band edge
    Tan, Ayse
    Kizilkaya, Serap
    Gunduz, Bayram
    Kara, Yunus
    ORGANIC COMMUNICATIONS, 2018, 11 (04) : 173 - 180
  • [35] Synthesis of Novel 2-Amino-benzo[de]isoquinolin-1,3-dione Derivatives
    Al-Salahi, R.
    Marzouk, M.
    ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (07) : 2166 - 2172
  • [36] Temperature-dependent behavior of the dual fluorescence of 2-(3-fluorophenyl)-2,3-dihydro-1H-benzo[f]isoindole-1,3-dione
    Valat, P
    Wintgens, V
    Kossanyi, J
    Biczòk, L
    Demeter, A
    Bérces, T
    HELVETICA CHIMICA ACTA, 2001, 84 (09) : 2813 - 2832
  • [37] SYNTHESIS OF 2-(DIPHENYLCYCLOPROPENYLIDENE)CYCLOBUTANE-1,3-DIONE (1,2-DIPHENYLBUTATRIAFULVALENE-3,5-DIONE)
    ASAO, T
    YAGIHARA, M
    KITAHARA, Y
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (03) : 1008 - 1009
  • [38] Synthesis and Herbicidal Activity of N-(4-Chloro-2-fluoro-5-substituted phenyl)isoindole-1,3-dione Derivatives
    Zhang, Hao
    Li, Qibo
    Liu, Kechang
    Liu, Ruiquan
    Li, Qingyang
    Wang, Qingmin
    Liu, Shangzhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (01) : 159 - 166
  • [39] ORGANOPHOSPHORUS COMPOUNDS .27. REACTION OF FLUORENYLIDENETRIPHENYLPHOSPHORANE AND TRIPHENYLPHOSPHINE WITH 2,3-BENZOFURANDIONE, BENZO[B]THIOPHENE-2,3-DIONE, AND NAPHTHO(2,1-B]FURAN-1,2-DIONE
    SIDKY, MM
    BOULOS, LS
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1978, 4 (03): : 299 - 302
  • [40] Microwave-assisted parallel synthesis of a 2-aryl-1H-isoindole-1,3-dione library
    Barchín, BM
    Cuadro, AM
    Alvarez-Builla, J
    SYNLETT, 2002, (02) : 343 - 345