Multicomponent Synthesis of 3(2H)-Furanones Initiated by Copper(II)-Catalyzed Alkyne-Carbonyl Cross Metathesis

被引：0
|
作者：
Su, Zhenjie [1 ]
Wang, Shaozhong [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Jiangsu Key Lab Adv Organ Mat, 163 Xianlin Ave, Nanjing 210023, Jiangsu, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 48期
基金：
中国国家自然科学基金;
关键词：
Multicomponent annulations; Alkyne-carbonyl metathesis; Cooperative catalysis; 3(2H)-furanone; EFFICIENT SYNTHESIS; BRONSTED ACID; CATALYZED SYNTHESIS; DOMINO REACTION; LEWIS-ACID; KETONES; COPPER; CYCLIZATION; NITRILES; STRATEGY;
D O I：
10.1002/chem.202401999
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The cooperative Lewis and Br & oslash;nsted acid catalysis makes convergent synthesis of 3(2H)-furanones through a three-component coupling of 1,3-diynes, alkyl glyoxylates and water. Control experiments support that Lewis acid-catalyzed highly chemo-, regio- and stereoselective alkyne-carbonyl metathesis of 1,3-diynes and alkyl glyoxylates might be the initial step of this multicomponent annulation. Further chemo- and regioselective hydration of the alkyne-carbonyl metathesis product and subsequent oxa-Michael addition promoted by Br & oslash;nsted acid results in the formation of two C-O bonds of the five-membered oxygen heterocycle.
引用
收藏
页数：6
相关论文
共 50 条
  • [1] Iron-Catalyzed Synthesis of Functionalized 2H-Chromenes via Intramolecular Alkyne-Carbonyl Metathesis
    Bera, Krishnendu
    Sarkar, Soumen
    Biswas, Srijit
    Maiti, Sukhendu
    Jana, Umasish
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) : 3539 - 3544
  • [2] Gold(I)-Catalyzed Ring-Closing Alkyne-Carbonyl Metathesis for the Synthesis of Butenolides
    Su, Zhenjie
    Amin, Pathan Mosim
    Wang, Shaozhong
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (65)
  • [3] Synthesis of Substituted Phenanthrene by Iron(III)-Catalyzed Intramolecular Alkyne-Carbonyl Metathesis
    Bera, Krishnendu
    Sarkar, Soumen
    Jalal, Swapnadeep
    Jana, Umasish
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) : 8780 - 8786
  • [4] Synthesis of 3(2H)-Furanones: A Review
    Omanakuttan, Vishnu K.
    John, Jubi
    Hopf, Henning
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (02) : 163 - 201
  • [5] Facile synthesis of 3(2H)-furanones
    Panda, Niranjan
    Nayak, Dinesh K.
    MONATSHEFTE FUR CHEMIE, 2018, 149 (06): : 1093 - 1100
  • [6] Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating
    Li, Wei -Le
    Liu, Bao-Yang
    Li, Chun-Mei
    Wang, Xiang
    Hao, Wen -Juan
    Jiang, Bo
    TETRAHEDRON LETTERS, 2024, 138
  • [7] Pyridinium triflate catalyzed intramolecular alkyne-carbonyl metathesis reaction of O-propargylated 2-hydroxyarylaldehydes
    Saini, Manoj Kumar
    Korawat, Harshita Singh
    Verma, Shashi Kant
    Basak, Ashok K.
    TETRAHEDRON LETTERS, 2020, 61 (52)
  • [8] Construction of 4-Acyl-2-quinolones through Sc(OTf)3-Catalyzed Ring-Closing Alkyne-Carbonyl Metathesis
    Su, Zhenjie
    Wang, Shaozhong
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24) : 16873 - 16881
  • [9] Iron-Catalyzed Intramolecular Alkyne-Carbonyl Metathesis: A New Cyclization Strategy for the Synthesis of Benzocarbazole and Azepino[1,2-a] indole Derivatives
    Paul, Kartick
    Jalal, Swapnadeep
    Kundal, Sandip
    Chakraborty, Baitan
    Jana, Umasish
    SYNTHESIS-STUTTGART, 2017, 49 (18): : 4205 - 4212
  • [10] Yb(OTf)3-Catalyzed Alkyne-Carbonyl Metathesis-Oxa-Michael Addition Relay for Diastereoselective Synthesis of Functionalized Naphtho[2,1-b]furans
    Xu, Ting
    Chen, Ke
    Zhu, Hong-Yu
    Hao, Wen-Juan
    Tu, Shu-Jiang
    Jiang, Bo
    ORGANIC LETTERS, 2020, 22 (06) : 2414 - 2418
12345