Phosphazene Base-Catalyzed Intramolecular Cascade Reactions of Aryl-Substituted Enynes

被引:2
|
作者
Tang, Jian-Sheng [1 ,2 ]
Xie, Ye-Xiang [1 ]
Wang, Zhi-Qiang [1 ]
Deng, Chen-Liang [1 ]
Li, Jin-Heng [1 ]
机构
[1] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Changsha 410081, Hunan, Peoples R China
[2] Hunan First Normal Univ, Math & Sci Dept, Changsha 410205, Hunan, Peoples R China
来源
SYNTHESIS-STUTTGART | 2010年 / 18期
基金
中国国家自然科学基金;
关键词
P(4)-t-Bu base; cascade cyclization reaction; 9-aryl-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one; 3-arylallyl; 3-arylpropiolate; DIELS-ALDER REACTIONS; ORGANIC-SYNTHESIS; DEPROTONATIVE FUNCTIONALIZATION; ARYLNAPHTHALENE LACTONES; AMMONIUM CATIONS; T-BU-P4; BASE; PROTIC MEDIA; CYCLOADDITIONS; CYCLIZATION; POLYAMINOPHOSPHAZENES;
D O I
10.1055/s-0030-1258172
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel method for the synthesis of 9-aryl-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-ones has been developed by P(4)-t-Bu-catalyzed intramolecular cascade reactions of enynes. In the presence of a catalytic amount of phosphazene P(4)-t-Bu base, a variety of 3-arylallyl 3-arylpropiolates underwent the cascade cyclization reaction smoothly in moderate to excellent yields.
引用
收藏
页码:3204 / 3210
页数:7
相关论文
共 50 条
  • [21] INTRAMOLECULAR GENERAL BASE-CATALYZED ALCOHOLYSIS OF AMIDES
    FIFE, TH
    BENJAMIN, BM
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (14) : 525 - 526
  • [22] Base-catalyzed intramolecular condensation of tokinolide B
    Quiroz-García, B
    Hernandez, L
    Toscano, RA
    Sterner, O
    Delgado, G
    TETRAHEDRON LETTERS, 2003, 44 (12) : 2509 - 2512
  • [23] A nickel-catalyzed carbozincation of aryl-substituted alkynes
    Stüdemann, T
    Ibrahim-Ouali, M
    Knochel, P
    TETRAHEDRON, 1998, 54 (07) : 1299 - 1316
  • [24] BASE-CATALYZED HYDROCARBON CONDENSATION REACTIONS
    HOFMANN, JE
    SCHRIESH.A
    ERDOL UND KOHLE ERDGAS PETROCHEMIE, 1968, 21 (02): : 104 - &
  • [25] BASE-CATALYZED REACTIONS OF ANTHRONES WITH DIENOPHILES
    RICKBORN, B
    KOERNER, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 332 - ORGN
  • [26] Silver Fluoride-Promoted Intramolecular Cascade Reactions of Enynes
    Tang, Jiansheng
    Xie, Yexiang
    Wang, Zhiqiang
    Li, Jinheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2011, 31 (05) : 653 - 658
  • [27] BASE-CATALYZED REACTIONS OF ANTHRONES WITH DIENOPHILES
    KOERNER, M
    RICKBORN, B
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09): : 2662 - 2672
  • [28] Alkynyl Group as Activating Group: Base-Catalyzed Diastereoselective Domino Reactions of Electron-Deficient Enynes
    Li, Wenbo
    Xiao, Yuanjing
    Zhang, Junliang
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3083 - 3088
  • [29] Highly efficient phosphazene base-catalyzed Michael addition of β-ketoesters in water
    Bensa, D
    Brunel, JM
    Buono, G
    Rodriguez, J
    SYNLETT, 2001, (05) : 715 - 717
  • [30] Phosphazene Base-Catalyzed Double Michael Addition: Stereoselective Synthesis of Cyclohexanones
    Li, Yang-Guo
    Zhang, Yang
    Du, Guang-Fen
    Gu, Cheng-Zhi
    He, Lin
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (01) : 76 - 80