Facile synthesis of 3(2H)-furanones

被引：6
|
作者：
Panda, Niranjan [1 ]
Nayak, Dinesh K. [1 ]
机构：
[1] Natl Inst Technol Rourkela, Dept Chem, Rourkela 769008, Odisha, India
来源：
MONATSHEFTE FUR CHEMIE | 2018年 / 149卷 / 06期
关键词：
3(2H)-furanones; 4-Hydroxyalkynone; Annulation; Cu-catalysis; Bullatenone; HIGHLY SUBSTITUTED 3(2H)-FURANONES; TERMINAL ALKYNES; ALPHA; BETA-ACETYLENIC KETONES; INTRAMOLECULAR CYCLIZATION; PROPARGYLIC ALCOHOLS; EFFICIENT SYNTHESIS; COUPLING REACTION; DOMINO REACTION; ACID-CHLORIDES; SIDE-CHAIN;
D O I：
10.1007/s00706-018-2152-8
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A practical method for the synthesis of 3(2H)-furanones including the bullatenone was described. Intramolecular cyclization of 4-hydroxyalkynones in the presence of KOH affords the biologically potent furanones in moderate-to-good yield at room temperature. Synthesis of 4-hydroxyalkynones from the reaction of acid chloride and terminal alkyne in the presence of copper iodide at room temperature was also reported. [GRAPHICS] .
引用
收藏
页码：1093 / 1100
页数：8
相关论文
共 50 条
  • [31] Study of the fragmentation of 3(2H)-furanones by mass spectrometry
    Fay, LB
    HuynhBa, T
    Blank, I
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (10) : 4057 - 4064
  • [32] PREPARATION AND TRANSFORMATIONS OF ALLENIC KETONES AND 3(2H)-FURANONES
    WOLFF, S
    AGOSTA, WC
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (11): : 2429 - 2434
  • [33] ANIONIC ACTIVATION BY FLUORIDE-ION IN SOLID-LIQUID SYSTEMS - SYNTHESIS OF 3(2H)-FURANONES AND 2 (5H)-FURANONES
    SEBTI, S
    FOUCAUD, A
    TETRAHEDRON, 1986, 42 (05) : 1361 - 1367
  • [34] 3(2H)-FURANONES FROM MERCURIC ACETATE OXIDATION OF ALLENIC KETONES - A SYNTHESIS OF BULLATENONE
    WOLFF, S
    AGOSTA, WC
    TETRAHEDRON LETTERS, 1985, 26 (06) : 703 - 704
  • [35] SYNTHESIS AND STEREOCHEMISTRY OF 2-BENZYLIDENE-4-CARBETHOXY-5-METHYL-3-(2H)-FURANONES
    ROCHAPITTA, ID
    SOCORROLACERDA, MD
    DUC, CL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (04) : 821 - 823
  • [36] ORGN 309-Catalytic asymmetric protocols for the enantioselective synthesis of 3(2H)-furanones
    Marson, Charles M.
    Edaan, Esra
    Morrell, James M.
    Coles, Simon J.
    Hursthouse, Michael B.
    Davies, David T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [37] Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols
    Yuan, Gaoqing
    He, Zaijun
    Zheng, Junhua
    Chen, Zhengwang
    Huang, Huawen
    Shi, Dabin
    Qi, Chaorong
    Jiang, Huanfeng
    TETRAHEDRON LETTERS, 2011, 52 (45) : 5956 - 5959
  • [38] Synthesis of Substituted 3(2H)-Furanones Using Alkylative Intramolecular Cyclization of Sulfonium Salts
    Inagaki, Sho
    Ukaku, Mika
    Chiba, Akira
    Takahashi, Fumi
    Yoshimi, Yasuharu
    Morita, Toshio
    Kawano, Tomikazu
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18): : 8363 - 8369
  • [39] SYNTHESIS OF TETRONIC ACID ENAMINE - DIENAMINE DERIVATIVES FROM 3-(2H)FURANONES
    CHANTEGREL, B
    GELIN, S
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (07) : 1335 - 1338
  • [40] Reaction of nitrile oxides with 3(2H)- and 2(5H)-furanones
    Lee, HW
    Kang, HY
    Lee, SJ
    Lee, IYC
    Lee, JH
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1996, 17 (07) : 595 - 599
12345