Synthesis of 3-arylphthalides with a quaternary carbon center via [4+1] cycloaddition of 2-carbonylcyclohexadienimines with isocyanides under metal-free conditions

被引：2
作者：
Du, Zhihao [1 ]
Xu, Qunjie [1 ,3 ]
Gu, Guangxin [2 ]
机构：
[1] Shanghai Univ Elect Power, Shanghai Engn Res Ctr Energy Saving Heat Exchange, Shanghai Key Lab Mat Protect & Adv Mat Elect Powe, Shanghai 200090, Peoples R China
[2] Fudan Univ, Dept Mat Sci, 220 Handan Rd, Shanghai 200433, Peoples R China
[3] Shanghai Inst Pollut Control & Ecol Secur, Shanghai 200092, Peoples R China
来源：
JOURNAL OF SAUDI CHEMICAL SOCIETY | 2020年 / 24卷 / 08期
关键词：
Isocyanides; Cycloaddition; Phthalide; Quaternary carbon center; Cascade reaction; DIRECTED ORTHO-METALATION; QUINONE IMINE KETALS; MULTICOMPONENT REACTIONS; ONE-POT; CYCLIZATION; PHTHALIDES; ACCESS; DEAROMATIZATION; ARYLATION; INSERTION;
D O I：
10.1016/j.jscs.2020.05.001
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Rapid synthesis of 3-arylphthalides with a quaternary carbon center has been achieved via a cascade [4+1] cycloaddition/nucleophilic 1,4-addition of 2-carbonylcyclohexadienimines with two molecules of isocyanides. The reaction proceeded smoothly under metal-free conditions leading to the formation of multi-functionalized phthalides in moderate to good yields. (C) 2020 The Author(s). Published by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码：545 / 551
页数：7
相关论文
共 75 条
  • [1] The Diels-Alder reactions of quinone imine ketals: A versatile synthesis of highly substituted 5-methoxyindoles
    Banfield, SC
    England, DB
    Kerr, MA
    [J]. ORGANIC LETTERS, 2001, 3 (21) : 3325 - 3327
  • [2] The structural diversity of phthalides from the Apiaceae
    Beck, John J.
    Chou, Shen-Chieh
    [J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (05): : 891 - 900
  • [3] DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION
    BERK, SC
    GROSSMAN, RB
    BUCHWALD, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8593 - 8601
  • [4] The cytosporones, new octaketide antibiotics isolated from an endophytic fungus
    Brady, SF
    Wagenaar, MM
    Singh, MP
    Janso, JE
    Clardy, J
    [J]. ORGANIC LETTERS, 2000, 2 (25) : 4043 - 4046
  • [5] Synthesis of 4-aminotropones from [(sulfinyl or sulfonyl)methyl]-substituted p-quinamines
    Carreno, M. Carmen
    Ortega-Guerra, Montserrat
    Ribagorda, Maria
    Sanz-Cuesta, M. Jesus
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (02) : 621 - 636
  • [6] A GaCl3-catalyzed [4+1] cycloaddition of α,β-unsaturated carbonyl compounds and isocyanides leading to unsaturated γ-lactone derivatives
    Chatani, N
    Oshita, M
    Tobisu, M
    Ishii, Y
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) : 7812 - 7813
  • [7] Phthalides from Pittosporum illicioides var. illicioides with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils
    Chou, Tsung-Hsien
    Chen, Ih-Sheng
    Hwang, Tsong-Long
    Wang, Tai-Chi
    Lee, Tzong-Huei
    Cheng, Lin-Yang
    Chang, Ya-Chih
    Cho, Jui-Ying
    Chen, Jih-Jung
    [J]. JOURNAL OF NATURAL PRODUCTS, 2008, 71 (10): : 1692 - 1695
  • [8] 4+1 RADICAL ANNULATIONS WITH ISONITRILES - A SIMPLE ROUTE TO CYCLOPENTA-FUSED QUINOLINES
    CURRAN, DP
    LIU, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) : 2127 - 2132
  • [9] Recent developments in isocyanide based multicomponent reactions in applied chemistry
    Dömling, A
    [J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
  • [10] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
12345678