Hypervalent iodine promoted transformation of 4H-chromenes into dihydrofurans and 2H-chromenes

被引:4
|
作者
Kale, Ashok [1 ,2 ]
Medishetti, Nagaraju [1 ,2 ]
Nanubolu, Jagadeesh Babu [2 ,3 ]
Atmakur, Krishnaiah [1 ,2 ]
机构
[1] CSIR Indian Inst Chem Technol, Fluoro & Agro Chem Dept, Hyderabad, India
[2] CSIR Indian Inst Chem Technol, Acad Sci & Innovat Res, Hyderabad, India
[3] CSIR Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad, India
关键词
1; 3-Diones; hypervalent iodine; 2H-chromenes; 4H-chromenes; dihydrofurans; DERIVATIVES; DESIGN; CONSTRUCTION; CYCLIZATION;
D O I
10.1080/00397911.2020.1799013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel protocol to synthetic transformation of 4H-chromenes into dihydrofurans (3) and 2H-chromenes (11) promoted by hypervalent iodine has been accomplished in a one-pot reaction at ambient temperature. Dihydrofurans are exclusively formed under basic reaction conditions, whereas, 2H-chromenes are the products under acidic condition. Simple reaction conditions with a broad substrate scope inclusive of various heterocycles and high yields are the attractive features of this protocol.
引用
收藏
页码:3264 / 3275
页数:12
相关论文
共 50 条
  • [41] Study on the reaction mechanism of Heck-oxyarylation of 2H-chromenes
    Kerti, Gabor
    Kurtan, Tibor
    Antus, Sandor
    [J]. ARKIVOC, 2009, : 103 - 110
  • [42] Oxidative rearrangement of 4H-chromenes to 2-aroylbenzofurans in the presence of selenium dioxide
    Maxim R. Demidov
    Marina Yu. Lapshina
    Dmitry V. Osipov
    Vitaly A. Osyanin
    Yuri N. Klimochkin
    [J]. Chemistry of Heterocyclic Compounds, 2017, 53 : 1053 - 1056
  • [43] Oxidative rearrangement of 4H-chromenes to 2-aroylbenzofurans in the presence of selenium dioxide
    Demidov, Maxim R.
    Lapshina, Marina Yu.
    Osipov, Dmitry V.
    Osyanin, Vitaly A.
    Klimochkin, Yuri N.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (09) : 1053 - 1056
  • [44] Photochromic properties of new benzoindene-fused 2H-chromenes
    Martins, CI
    Coelho, PJ
    Carvalho, LM
    Oliveira-Campos, AMF
    Samat, A
    Guglielmetti, R
    [J]. HELVETICA CHIMICA ACTA, 2003, 86 (03) : 570 - 578
  • [45] SIMPLE AND RAPID PROCEDURE FOR THE SYNTHESIS OF SOME NEW 2H-CHROMENES
    Zonouzi, A.
    Googheri, M. Sadeghi
    Miralinaghi, P. S.
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2008, 40 (05) : 471 - 477
  • [46] Acid-Promoted Cascade Reaction of 4H-Chromenes: Access to Hexahydronapthalenes via Decarboxylative Intramolecular Cyclization
    Kale, Ashok
    Medishetti, Nagaraju
    Babu Nanubolu, Jagadeesh
    Atmakur, Krishnaiah
    [J]. CHEMISTRYSELECT, 2021, 6 (05): : 983 - 986
  • [47] Iron-Catalyzed Rearrangements and Cycloaddition Reactions of 2H-Chromenes
    Luan, Yi
    Sun, Huan
    Schaus, Scott E.
    [J]. ORGANIC LETTERS, 2011, 13 (24) : 6480 - 6483
  • [48] Furo-fused 2H-chromenes: Synthesis and photochromic properties
    Pozzo, JL
    Samat, A
    Guglielmetti, R
    Lokshin, V
    Minkin, V
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1996, 74 (09) : 1649 - 1659
  • [49] Synthesis of Dihydropyrrole Derivatives by Oxidative Functionalization of 2-Amino-4H-Chromenes Using Hypervalent Iodine Reagents
    Indukuri, Divakar Reddy
    Potuganti, Gal Reddy
    Nanubolu, Jagadeesh Babu
    Alla, Manjula
    [J]. SYNLETT, 2021, 32 (11) : 1109 - 1116
  • [50] The Effect of Terminal Bromoalkoxy Substituents on the Photochromism of Functionalized 2H-Chromenes
    Chernikova, Ekaterina Y. Y.
    Perevozchikova, Polina S. S.
    Shepel, Nikolai E. E.
    Fedorova, Olga A. A.
    Fedorov, Yuri V. V.
    [J]. CHEMPHOTOCHEM, 2023, 7 (04)