Synthesis of 4H-chromenes by silver(Ⅰ)-catalyzed cycloaddition of ortho-quinone methides with N-allenamides

被引：0
|
作者：
Long Kong [1 ]
Nuligonda Thirupathi [1 ]
Jiong Jia [1 ]
Zhenghu Xu [1 ,2 ]
机构：
[1] Key Laboratory for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University
[2] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
来源：
Science China(Chemistry) | 2019年 / 01期
基金：
中国国家自然科学基金;
关键词：
4H-chromene; ortho-quinone methide; N-allenamide; silver-catalysis; cycloaddition;
D O I：
暂无
中图分类号：
O621.3 [有机合成化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chromenes represent an important class of six-membered heterocycles and have drawn tremendous attention in recent years. In this article, we report a convenient and practical synthesis of this heterocycle by a silver(I)-catalyzed cycloaddition reaction between in situ generated ortho-quinone methides and N-allenamides. Diverse 4H-chromenes were synthesized in good to excellent yields under very mild conditions.
引用
收藏
页码：80 / 86
页数：7
相关论文
共 50 条
  • [31] Enantioselective Synthesis of Chromanes by Iridium-Catalyzed Asymmetric Hydrogenation of 4H-Chromenes
    Valla, Carine
    Baeza, ALejandro
    Menges, Frederik
    Pfaltz, Andreas
    SYNLETT, 2008, (20) : 3167 - 3171
  • [32] Cinchona Alkaloid Catalyzed Enantioselective [4+2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans
    Deng, Yu-Hua
    Chu, Wen-Dao
    Zhang, Xiang-Zhi
    Yan, Xu
    Yu, Ke-Yin
    Yang, Liang-Liang
    Huang, Hanmin
    Fan, Chun-An
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10): : 5433 - 5440
  • [33] Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4+2] Cycloaddition Reaction
    Wang, Shu
    Liang, Ge
    Wang, Cheng
    Wang, Chen-Hong
    Huang, Zhiyuan
    Tung, Chen-Ho
    Wu, Li-Zhu
    ORGANIC LETTERS, 2024, 27 (01) : 470 - 475
  • [34] Synthesis of β-vinyl-substituted 4H-chromenes and [4+2] cycloaddition reactions involving them
    Irina A. Semenova
    Dmitry V. Osipov
    Pavel E. Krasnikov
    Vitaly A. Osyanin
    Yuri N. Klimochkin
    Chemistry of Heterocyclic Compounds, 2023, 59 : 260 - 266
  • [35] Synthesis of β-vinyl-substituted 4H-chromenes and [4+2] cycloaddition reactions involving them
    Semenova, Irina A. A.
    Osipov, Dmitry V. V.
    Krasnikov, Pavel E. E.
    Osyanin, Vitaly A. A.
    Klimochkin, Yuri N. N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (4-5) : 260 - 266
  • [36] Diastereodivergent Asymmetric [4+2] Cycloaddition of In Situ Generated ortho-Quinone Methides and Allenyl Ketones Enabled by Chiral Phosphoric Acid Catalysis
    Shen, Guosong
    He, Faqian
    Xie, Wansen
    Gu, Huanchao
    Yang, Xiaoyu
    ACS CATALYSIS, 2023, 13 (19) : 12472 - 12480
  • [37] A visible light photoredox catalyzed carbon radical-mediated generation of ortho-quinone methides for 2,3-dihydrobenzofuran synthesis
    Zhou, Fan
    Cheng, Ying
    Liu, Xiao-Peng
    Chen, Jia-Rong
    Xiao, Wen-Jing
    CHEMICAL COMMUNICATIONS, 2019, 55 (21) : 3117 - 3120
  • [38] Catalytic Asymmetric [4+2] Cycloaddition of ortho-Alkenyl Naphthols/Phenols with ortho-Quinone Methides: Highly Stereoselective Synthesis of Chiral 2,3,4-Trisubstituted Chromans
    Feng, Shubo
    Yang, Binmiao
    Chen, Tao
    Wang, Ran
    Deng, Yu-Hua
    Shao, Zhihui
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5231 - 5244
  • [39] A Novel Method to Construct 2-Aminobenzofurans via [4+1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides
    Lin, Huaxin
    Tang, Senling
    Pan, Yang
    Liang, Peng
    Ma, Xiaofeng
    Jiao, Wei
    Shao, Huawu
    MOLECULES, 2022, 27 (23):
  • [40] Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of 4H-Chromenes and Naphthalenes
    Malakar, Chandi C.
    Schmidt, Dietmar
    Conrad, Juergen
    Beifuss, Uwe
    ORGANIC LETTERS, 2011, 13 (08) : 1972 - 1975
12345