Unexpected tandem ylide annulation reaction for controllable synthesis of 2H-chromenes and 4H-chromenes

被引:102
|
作者
Ye, Long-Wu [1 ]
Sun, Xiu-Li [1 ]
Zhu, Chun-Yin [1 ]
Tang, Yong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ol0615174
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unexpected tetrahydrothiophene-catalyzed ylide annulation reaction, via tandem Michael addition/elimination/substitution, for the controllable synthesis of 2H-chromenes and 4H-chromenes has been developed.
引用
收藏
页码:3853 / 3856
页数:4
相关论文
共 50 条
  • [1] An efficient regioselective reaction of indole with 2H-chromenes for the synthesis of new 4H-chromenes in environmentally benign media
    Rao, L. Chandrasekhara
    Kumar, N. Satish
    Babu, N. Jagadeesh
    Meshram, H. M.
    [J]. TETRAHEDRON LETTERS, 2014, 55 (38) : 5342 - 5346
  • [2] Hypervalent iodine promoted transformation of 4H-chromenes into dihydrofurans and 2H-chromenes
    Kale, Ashok
    Medishetti, Nagaraju
    Nanubolu, Jagadeesh Babu
    Atmakur, Krishnaiah
    [J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (21) : 3264 - 3275
  • [3] A CONVENIENT SYNTHESIS OF 4H-CHROMENES
    ROUDIER, JF
    FOUCAUD, A
    [J]. SYNTHESIS-STUTTGART, 1984, (02): : 159 - 160
  • [4] Catalytic Synthesis of 2H-Chromenes
    Majumdar, Nilanjana
    Paul, Nanda D.
    Mandal, Sutanuva
    de Bruin, Bas
    Wulff, William D.
    [J]. ACS CATALYSIS, 2015, 5 (04): : 2329 - 2366
  • [5] Synthesis of Chromanes and 4H-Chromenes: Exploring the Oxidation of 2H-Chromenes and Dihydro-1-benzoxepines by Hypervalent Iodine(III)
    Ahmad, Anees
    Silva, Luiz F., Jr.
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (23): : 3671 - 3677
  • [6] Electrospray tandem mass spectrometry of 2H-chromenes
    Domingues, MRM
    Domingues, P
    Oliveira, MM
    Carvalho, LHM
    Oliveira-Campos, AF
    Correia, AJF
    [J]. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2004, 18 (24) : 2969 - 2975
  • [7] Synthesis of 2H-Chromenes via Unexpected [4+2] Annulation of Alkynyl Thioethers with o-Hydroxybenzyl Alcohols
    Bu, Hao-Zhen
    Li, Hang-Hao
    Luo, Wen-Feng
    Luo, Chen
    Qian, Peng-Cheng
    Ye, Long-Wu
    [J]. ORGANIC LETTERS, 2020, 22 (02) : 648 - 652
  • [8] A facile approach for the synthesis of novel substituted 4H-chromenes and condensation reactions of 4H-chromenes leading to chromenopyrrolones and triazolylchromenopyrrolones
    Saidachary, Gannerla
    Prasad, Kasagani Veera
    Sairam, Mudulkar
    Raju, Bhimapaka China
    [J]. TETRAHEDRON LETTERS, 2014, 55 (34) : 4753 - 4757
  • [9] Synthesis of 2H-chromenes in ionic liquid solvents
    Kabalka, GW
    Venkataiah, B
    Das, BC
    [J]. SYNLETT, 2004, (12) : 2194 - 2196
  • [10] Synthesis of 2H-chromenes: recent advances and perspectives
    Zheng, Shi-Lu
    Chen, Long
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (48) : 10530 - 10548