Synthesis of Cyclohepta[b]indoles and Furo[3,4-b]carbazoles from Indoles, Tertiary Propargylic Alcohols, and Activated Alkynes

被引：8
|
作者：
Yin, Hailing [1 ]
Wu, Yunjun [1 ]
Jiang, Yifan [1 ]
Wang, Meifang [1 ,2 ]
Wang, Shaoyin [1 ,2 ]
机构：
[1] Wannan Med Coll, Inst Synth & Applicat Med Mat, Dept Chem, Wuhu, Anhui, Peoples R China
[2] Anhui Med Univ, Key Lab Antiinflammatory & Immune Med, Minist Educ, Hefei 230032, Anhui, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 17期
关键词：
CARBAZOLE ALKALOIDS; 4+3 CYCLOADDITION; GOLD CATALYSIS; DERIVATIVES; ACCESS;
D O I：
10.1021/acs.orglett.3c00885
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A robust metal-free and environmentally friendly approach to cyclohepta[b]indole and furo[3,4-b]carbazole frameworks via a three-component reaction from indoles, tertiary propargylic alcohols, and activated alkynes is described. A probable mechanism was proposed on the basis of the isolation and characterization of a key intermediate of the reaction. A gram-scale reaction and product derivatizations were also performed to demonstrate the practicality of the developed methodology.
引用
收藏
页码：3078 / 3082
页数：5
相关论文
共 50 条
  • [1] Synthesis of hexahydroazonino[5,6-b]indoles from hexahydroazepino[4,3-b]-and-[3,4-b]indoles and activated alkynes
    L. G. Voskressensky
    S. V. Akbulatov
    T. N. Borisova
    A. V. Kleimenov
    A. V. Varlamov
    Russian Chemical Bulletin, 2007, 56 : 2323 - 2329
  • [2] Synthesis of hexahydroazonino[5,6-b]indoles from hexahydroazepino[4,3-b]-and-[3,4-b]indoles and activated alkynes
    Voskressensky, L. G.
    Akbulatov, S. V.
    Borisova, T. N.
    Kleimenov, A. V.
    Varlamov, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (11) : 2323 - 2329
  • [3] Synthesis of bis-4H-furo[3,4-b]indoles
    McGowan, Meredeth A.
    Perreault, Denise M.
    Thornton, Nancy B.
    Garaas, Sarah D.
    Gribble, Gordon W.
    ARKIVOC, 2018, : 334 - 347
  • [4] Intramolecular Cycloaddition Reactions of Furo[3,4-b]indoles for Alkaloid Synthesis
    Padwa, Albert
    Zou, Yan
    Cheng, Bo
    Li, Hao
    Downer-Riley, Nadale
    Straub, Christopher S.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07): : 3173 - 3184
  • [5] Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides
    Chen, Weiliang
    Xia, Yong
    Lin, Lili
    Yuan, Xiao
    Guo, Songsong
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (43) : 15104 - 15107
  • [6] SYNTHESIS OF PYRIDO[3,4-B]PYRANO[3,4-B]INDOLES
    FRETER, K
    FUCHS, V
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) : 377 - 379
  • [7] SYNTHESIS OF DIHYDROTHIENO[3,4-B]INDOLES
    KOGAN, NA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1977, (10): : 1327 - 1331
  • [8] REACTION OF INDOLES WITH ALDEHYDES - SYNTHESIS OF DIHYDROPYRROLO[3,4-B]INDOLES
    KOGAN, NA
    VLASOVA, MI
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1976, (11): : 1516 - 1523
  • [9] SYNTHESIS AND DIELS-ALDER REACTIONS OF FURO [3,4,-B] INDOLES - A NEW SYNTHESIS OF CARBAZOLES
    KEAVY, DJ
    GRIBBLE, GW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 191 : 318 - ORGN
  • [10] DIHYDROPYRROLO[3,4-B]-INDOLES AND DIHYDROPYRIMIDO[4,5-B]INDOLES
    VLASOVA, MI
    KOGAN, NA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1982, (07): : 935 - 939
12345