Gold-catalyzed synthesis of 1H-isochromene-4-carbaldehydes via oxidative cascade cyclization

被引:11
|
作者
Raju, Chittala Emmaniel [1 ,2 ]
Kadiyala, Veerabhushanam [1 ,2 ]
Sreenivasulu, Gottam [1 ,2 ]
Kumar, Perla Bharath [1 ,2 ]
Sridhar, Balasubramanian [3 ]
Karunakar, Galla, V [1 ,2 ]
机构
[1] CSIR Indian Inst Chem Technol, Fluoro & Agrochem Dept, Hyderabad 500007, Andhra Pradesh, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
[3] CSIR Indian Inst Chem Technol, Ctr Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India
关键词
INTRAMOLECULAR CYCLIZATION; MANSONONE-F; DERIVATIVES; HYDROGENATION; ACTIVATION; DISCOVERY;
D O I
10.1039/d1ob00066g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient gold-catalyzed formation of indenylidene-derived 1H-isochromene-4-carbaldehydes from substituted 1,5,10-triyne-O-silanes was developed under mild reaction conditions. In this reaction, gold-catalyzed selective oxidation, 1,2-migration, nucleophilic addition and then 5-endo-dig cyclization took place regioselectively. The indenylidene-derived isochromene-4-carbaldehydes were synthesized in moderate to very good yields via the formation of new C-C and C-O bonds in one pot.
引用
收藏
页码:3634 / 3643
页数:10
相关论文
共 50 条
  • [1] Gold-Catalyzed Cascade Oxidative Cyclization and Arylation of Allenoates
    Zhang, Rui
    Xu, Qin
    Chen, Kai
    Gu, Peng
    Shi, Min
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (32) : 7366 - 7371
  • [2] Synthesis of Substituted Quinolizidines via a Gold-Catalyzed Double Cyclization Cascade
    Nonaka, Shiori
    Sugimoto, Kenji
    Ueda, Hirofumi
    Tokuyama, Hidetoshi
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (03) : 380 - 385
  • [3] Gold-Catalyzed Cascade Cyclization-Oxidative Alkynylation of Allenoates
    Hopkinson, Matthew N.
    Ross, Jonathan E.
    Giuffredi, Guy T.
    Gee, Antony D.
    Gouverneur, Veronique
    [J]. ORGANIC LETTERS, 2010, 12 (21) : 4904 - 4907
  • [4] Stereoselective synthesis of tetracyclic indolines via gold-catalyzed cascade cyclization reactions
    Cera, Gianpiero
    Crispino, Pasquale
    Monari, Magda
    Bandini, Marco
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (27) : 7803 - 7805
  • [5] Efficient synthesis of tetracyclic γ-lactams via gold-catalyzed oxidative cyclization of alkenyl diynes
    Shi, Chong-Yang
    Zhou, Ji-Jia
    Hong, Pan
    Zhu, Bo-Han
    Hong, Feng-Lin
    Qian, Peng-Cheng
    Sun, Qing
    Lu, Xin
    Ye, Long-Wu
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (09): : 2557 - 2562
  • [6] Direct Synthesis of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Diynes
    Hirano, Kimio
    Inaba, Yusuke
    Takahashi, Naoya
    Shimano, Masanao
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05): : 1212 - 1227
  • [7] Gold-Catalyzed Oxidative Cascade Cyclization of 1,3-Diynamides: Polycyclic N-Heterocycle Synthesis via Construction of a Furopyridinyl Core
    Liu, Jibing
    Zhu, Lei
    Wan, Wan
    Huang, Xueliang
    [J]. ORGANIC LETTERS, 2020, 22 (08) : 3279 - 3285
  • [8] Total Synthesis of Dictyodendrins by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles
    Matsuoka, Junpei
    Matsuda, Yuka
    Kawada, Yuiki
    Oishi, Shinya
    Ohno, Hiroaki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (26) : 7444 - 7448
  • [9] Gold-Catalyzed Oxidative Cyclization of Chiral Homopropargyl Amides: Synthesis of Enantioenriched γ-Lactams
    Shu, Chao
    Liu, Meng-Qi
    Wang, Shan-Shan
    Li, Long
    Ye, Long-Wu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07): : 3292 - 3299
  • [10] Synthesis of Benzofuran Derivates via a Gold-Catalyzed Claisen Rearrangement Cascade
    Li, Yankun
    Tung, Chen -Ho
    Xu, Zhenghu
    [J]. ORGANIC LETTERS, 2022, 24 (31) : 5829 - 5834