Synthesis of Substituted 1,4,5,6-Tetrahydrocyclopenta[b]pyrroles by Platinum-Catalyzed Cascade Cyclization/Ring Expansion of 2-Alkynyl-1-azaspiro[2.3]hexanes

被引:32
|
作者
Yoshida, Masahiro [1 ]
Maeyama, Yohei [1 ]
Al-Amin, Mohammad [1 ]
Shishido, Kozo [1 ]
机构
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 14期
基金
日本学术振兴会;
关键词
EFFICIENT SYNTHESIS; PYRROLES; GOLD; ACTIVATION; OXIDATION; ALKENES; TOOL;
D O I
10.1021/jo201000f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 2-allcynyl-1-azaspiro[2.3]hexanes with a platinum catalyst is described. 1,4,5,6-Tetrahydrocyclopenta[b]pyrroles having a variety of substituents were conveniently synthesized via a cascade cyclization/ring-expansion process.
引用
收藏
页码:5813 / 5820
页数:8
相关论文
共 25 条
  • [1] An Au(I)-catalyzed rearrangement/cyclization cascade toward the synthesis of 2-substituted-1,4,5,6-tetrahydrocyclopenta[b]pyrrole
    Mou, Xue-Qing
    Xu, Zheng-Liang
    Wang, Shao-Hua
    Zhu, Dao-Yong
    Wang, Jie
    Bao, Wen
    Zhou, Shi-Jiang
    Yang, Chao
    Zhang, Di
    CHEMICAL COMMUNICATIONS, 2015, 51 (60) : 12064 - 12067
  • [2] An improved method for the preparation of N-unsubstituted 1,4,5,6-tetrahydrocyclopenta[b]pyrroles: Synthesis of an azaprostacyclin analogue and its 7-cyano derivative
    Rousseau, B
    Nydegger, F
    Gossauer, A
    BennuaSkalmowski, B
    Vorbruggen, H
    SYNTHESIS-STUTTGART, 1996, (11): : 1336 - &
  • [3] Zn(OTf)2-Catalyzed Synthesis of 2-Alkynylazetidines and their Ring Expansion to Functionalized 1,4,5,6-Tetrahydropyridines
    Shehzadi, Syeda Aaliya
    Kushwaha, Khushbu
    Sterckx, Hans
    Tehrani, Kourosch Abbaspour
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (22) : 4393 - 4401
  • [4] Platinum-Catalyzed Cyclization/[1,2]-Alkyl Migration/Allyl Shift/Cyclization Cascade of Epoxy Alkynyl Allyl Ethers: A Step-Economical Route to Spirobenzo[h]chromanones
    Yang, Yan-Fang
    Shu, Xing-Zhong
    Luo, Jian-Yi
    Ali, Shaukat
    Liang, Yong-Min
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (28) : 8600 - 8604
  • [5] Platinum(IV)-Catalyzed Regioselective Synthesis of Highly Substituted 4H-Cyclopenta[b]furans via Cascade Hetero- cyclization of 2-(1-Alkynyl)-3-aryl-2-propenals with Arylethenes
    He, Ting
    Gao, Pin
    Zhao, Shu-Chun
    Shi, You-Di
    Liu, Xue-Yuan
    Liang, Yong-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) : 365 - 369
  • [6] Synthesis of Fully Substituted 3-Formyl-4-iodofurans via a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization/Iodination Cascade
    Wang, Tao
    Shi, Shuai
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (10) : 2337 - 2342
  • [7] Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of 2-(1-alkynyl)benzaldimines
    Dai, GX
    Larock, RC
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7042 - 7047
  • [8] A Copper-Catalyzed N-Alkynylation Route to 2-Substituted N-Alkynyl Pyrroles and Their Cyclization into Pyrrolo[2,1-c]oxazin-1-ones: A Formal Total Synthesis of Peramine
    Reinus, Brandon J.
    Kerwin, Sean M.
    SYNTHESIS-STUTTGART, 2017, 49 (11): : 2544 - 2554
  • [9] One-pot B(C6F5)3 catalyzed cascade synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones
    Shinde, Achut R.
    Mane, Yogesh D.
    Muley, Dnyanoba B.
    SYNTHETIC COMMUNICATIONS, 2020, 50 (01) : 33 - 40
  • [10] Synthesis of a novel heterocyclic ring system: 4-substituted-1-thioxo[1,2,4,5]tetraazino[1,2-b]phtalazine-6,11-dione
    Amin, Amir H.
    Bakherad, Mohammad
    HETEROCYCLIC COMMUNICATIONS, 2007, 13 (05) : 311 - 314