Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes

被引：265
|
作者：
Movassaghi, M [1 ]
Hill, MD [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 14期
关键词：
D O I：
10.1021/ja060626a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We describe a two-step conversion of various N-vinyl and N-aryl amides to the corresponding substituted pyridines and quinolines, respectively. The process involves the direct conversion of amides, including sensitive N-vinyl amides, to the corresponding trimethylsilyl alkynyl imines followed by a ruthenium-catalyzed protodesilylation and cycloisomerization. A wide range of new alkynyl imines are prepared and readily converted to the corresponding azaheterocycles. Copyright © 2006 American Chemical Society.
引用
收藏
页码：4592 / 4593
页数：2
相关论文
共 50 条
  • [1] Ruthenium-Catalyzed Cycloisomerization and Its Application to the Synthesis of (±)-Cinchonaminone
    Ogawa, Takao
    Nakamura, Tomonori
    Araki, Takuya
    Yamamoto, Koujirou
    Shuto, Satoshi
    Arisawa, Mitsuhiro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (16) : 3084 - 3087
  • [2] Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization
    Havare, Nizam
    TURKISH JOURNAL OF CHEMISTRY, 2020, 44 (06) : 1445 - +
  • [3] RUTHENIUM-CATALYZED SYNTHESIS OF 1-SUBSTITUTED-3-HYDROXYPERHYDROAZEPINES
    YOUN, YZ
    LEE, DY
    WOO, BW
    SHIM, JG
    CHAE, SA
    SHIM, SC
    JOURNAL OF MOLECULAR CATALYSIS, 1993, 79 (1-3): : 39 - 45
  • [4] Synthesis of the putative structure of fistulosin using the ruthenium-catalyzed cycloisomerization of diene
    Terada, Y
    Arisawa, M
    Nishida, A
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03): : 1269 - 1272
  • [5] Application of a Ruthenium-Catalyzed Allylation-Cycloisomerization Cascade to the Synthesis of (±)-Herbindole A
    Thies, Nora
    Sturminger, Martin
    Haak, Edgar
    SYNLETT, 2017, 28 (06) : 701 - 704
  • [6] Ruthenium-Catalyzed Cycloisomerization of 2-Alkynylanilides: Synthesis of 3-Substituted Indoles by 1,2-Carbon Migration
    Watanabe, Takuma
    Mutoh, Yuichiro
    Saito, Shinichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) : 7749 - 7752
  • [7] Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium-Catalyzed Alkyne Cyclotrimerizations
    Foster, Robert W.
    Tame, Christopher J.
    Hailes, Helen C.
    Sheppard, Tom D.
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2353 - 2360
  • [8] An unusual ruthenium-catalyzed cycloisomerization of alkynes and propargyl alcohols
    Trost, BM
    Rudd, MT
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) : 4178 - 4179
  • [9] An unusual ruthenium-catalyzed cycloisomerization of alkynes and propargyl alcohols
    Trost, Barry M.
    Rudd, Michael T.
    1600, American Chemical Society (124):
  • [10] RUTHENIUM-CATALYZED SYNTHESIS OF 1-SUBSTITUTED PERHYDROAZEPINES
    SHIM, SC
    DOH, CH
    WOO, BW
    KIM, HS
    HUH, KT
    PARK, WH
    LEE, H
    JOURNAL OF MOLECULAR CATALYSIS, 1990, 62 (02): : L11 - L15
12345