A Synthesis of Dihydrofuran-3(2H)-ones

被引：10
|
作者：
Tata, Rama Rao [1 ]
Harmata, Michael [1 ]
机构：
[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 13期
关键词：
MICHAEL ADDITION-REACTIONS; ALGA LAURENCIA-CHILENSIS; STEREOSELECTIVE-SYNTHESIS; RING-CLOSURE; SUBSTITUTED TETRAHYDROFURANS; 5-ENDO-TRIG CYCLIZATION; GEIPARVARIN ANALOGS; GEIJERA-PARVIFLORA; XYLARIA-LONGIANA; DERIVATIVES;
D O I：
10.1021/acs.joc.5b01076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of readily available alpha '-hydroxyenones with a catalytic amount of strong acid in refluxing toluene affords the corresponding dihydrofuran-3(2H)-ones in excellent yields via a formal 5-endo-trig cyclization.
引用
收藏
页码：6839 / 6845
页数：7
相关论文
共 50 条
  • [1] A catalytic synthesis of dihydrofuran-3(2H)-imine skeletons from isocyanides, terminal alkynes, and oxiranes
    Samzadeh-Kermani, Alireza
    Poorhabibi-Zarandi, Marjan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (04) : 1901 - 1911
  • [2] Synthesis of 2,5-Disubstituted Dihydrofuran-3(2H)-ones via [2,3]-Sigmatropic Rearrangement of Oxonium Ylides Generated from α-Oxo Gold Carbenes
    Han, Miyeon
    Bae, Joohee
    Choi, Juhee
    Tae, Jinsung
    SYNLETT, 2013, 24 (16) : 2077 - 2080
  • [3] Regio- and Chemoselective Synthesis of 3-(Dihydrofuran-3(2H)-ylidene)isobenzofuran-1(3H)-imines via Tandem Alkynyl Prins- and Intramolecular Oxycyclization Reactions
    Shit, Sudip
    Behera, Bipin Kumar
    Biswas, Subhamoy
    Saikia, Anil K. K.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15) : 10844 - 10857
  • [4] Synthesis of Functionalized Pyridazin-3(2H)-ones via Bromine-Magnesium Exchange on Bromopyridazin-3(2H)-ones
    Ryabtsova, Oxana
    Verhelst, Tom
    Baeten, Mattijs
    Velde, Christophe M. L. Vande
    Maes, Bert U. W.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) : 9440 - 9445
  • [5] Synthesis of (Hetero)arylated Pyridazin-3(2H)-ones via Negishi Reaction Involving Zincated Pyridazin-3(2H)-ones
    Verhelst, Tom
    Liu, Zuming
    Maes, Jens
    Maes, Bert U. W.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) : 9648 - 9659
  • [6] Microwave-Assisted Synthesis of Benzofuran-3(2H)-ones
    Hu, Xiaojing
    Lai, Huimin
    Zhao, Fangfei
    Hu, Shuyu
    Sun, Qianqian
    Fang, Lizhen
    ACTA CHIMICA SLOVENICA, 2019, 66 (03) : 745 - 750
  • [7] Efficient and Convenient Synthesis of Indazol-3(2H)-ones and 2-Aminobenzonitriles
    Dou, Guolan
    Shi, Daqing
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (06): : 1073 - 1077
  • [8] The synthesis of phthalazin-1(2H)-ones and 3-hydroxyisobenzofuran-1(3H)-ones via the ring contraction of tropones
    Li, Wenjuan
    Li, Haijun
    Li, Zhiping
    TETRAHEDRON LETTERS, 2010, 51 (41) : 5448 - 5450
  • [9] Synthesis, cytotoxic activity, and tubulin polymerization inhibitory activity of new pyrrol-2(3H)-ones and pyridazin-3(2H)-ones
    Abbas, Samar Hafez
    Abuo-Rahma, Gamal El-Din A. A.
    Abdel-Aziz, Mohamed
    Aly, Omar M.
    Beshr, Eman A.
    Gamal-Eldeen, Amira M.
    BIOORGANIC CHEMISTRY, 2016, 66 : 46 - 62
  • [10] Synthesis of Functionalized Pyridazin-3(2H)-ones via Nucleophilic Substitution of Hydrogen (SNH)
    Verhelst, Tom
    Verbeeck, Stefan
    Ryabtsova, Oxana
    Depraetere, Stefaan
    Maes, Bert U. W.
    ORGANIC LETTERS, 2011, 13 (02) : 272 - 275
12345