Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases

被引:24
|
作者
Carpita, Adriano [2 ]
Ribecai, Arianna [1 ]
机构
[1] GlaxoSmithKline SpA, Chem Dev Dept, I-37135 Verona, Italy
[2] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
关键词
Indoles; Water; Cycloisomerization; Microwaves; 2-Alkynylanilines; Green chemistry; ONE-POT SYNTHESIS; NEAR-CRITICAL WATER; 2-ETHYNYLANILINE DERIVATIVES; INTRAMOLECULAR HYDROAMINATION; 2-SUBSTITUTED INDOLES; CYCLIZATION REACTIONS; CONVENIENT SYNTHESIS; TERMINAL ALKYNES; ARYL IODIDES; PALLADIUM;
D O I
10.1016/j.tetlet.2009.09.135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented green methodology is described for the preparation of differently substituted indoles via microwave-assisted cycloisomerization of 2-alkynylaniline derivatives in water. Moderate to good yields in the cyclization can be achieved for a variety of 2-aminoaryl alkynes. Reactions are run without any added metal catalyst, acid, or base, and do not take place by applying conventional heating. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6877 / 6881
页数:5
相关论文
共 50 条
  • [1] Microwave-assisted synthesis of indole- and azaindole-derivatives in water via cycloisomerization of 2-alkynylanilines and alkynylpyridinamines promoted by amines or catalytic amounts of neutral or basic salts
    Carpita, Adriano
    Ribecai, Arianna
    Stabile, Paolo
    TETRAHEDRON, 2010, 66 (35) : 7169 - 7178
  • [2] Microwave-assisted synthesis of phenylpyrimidine derivatives via Suzuki-Miyaura reactions in water
    Le, Yi
    Zhang, Yan
    Wang, Qin
    Rao, Nian
    Li, Dan
    Liu, Li
    Ouyang, Guiping
    Yan, Longjia
    TETRAHEDRON LETTERS, 2021, 68
  • [3] Microwave-Assisted Synthesis of 3-Substituted Indole Derivatives via Three-Component Domino Reaction
    Lin, Wei
    Hu, Xiuxiu
    Wang, Yazhen
    Song, Shuai
    Zhang, Mengye
    Shi, Daqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (04) : 855 - 862
  • [4] Unexpected and Green Synthesis of Azapodophyllotoxin Derivatives via Microwave-Assisted Multicomponent Reactions in Ammonia Water
    Shi, Feng
    Ma, Ning
    Zhang, Yan
    Zhang, Ge
    Jiang, Bo
    Tu, Shujiang
    SYNTHETIC COMMUNICATIONS, 2010, 40 (02) : 235 - 241
  • [5] MICROWAVE-ASSISTED SYNTHESIS OF 2-AMINOTHIOPHENE DERIVATIVES VIA IMPROVED GEWALD REACTIONS
    Ruan, Bankang
    Zhang, Zhiyan
    Huang, Lei
    Xu, Chao
    Li, Luolan
    HETEROCYCLES, 2021, 102 (10) : 2007 - 2018
  • [6] Microwave-Assisted Synthesis of 2-Methyl-1H-indole-3-carboxylate Derivatives via Pd-Catalyzed Heterocyclization
    Bellavita, Rosa
    Casertano, Marcello
    Grasso, Nicola
    Gillick-Healy, Malachi
    Kelly, Brian G.
    Adamo, Mauro F. A.
    Menna, Marialuisa
    Merlino, Francesco
    Grieco, Paolo
    SYMMETRY-BASEL, 2022, 14 (03):
  • [7] Microwave-Assisted Regioselective Synthesis of 3-Functionalized Indole Derivatives via Three-Component Domino Reaction
    Lin, Wei
    Zheng, Yong-Xiang
    Xun, Zhan
    Huang, Zhi-Bin
    Shi, Da-Qing
    ACS COMBINATORIAL SCIENCE, 2017, 19 (11) : 708 - 713
  • [8] Microwave-assisted synthesis of Schiff's bases of 1,2,4-triazole derivatives and their anthelmintic activity
    Sahoo, Biswa Mohan
    Nagamounika, K.
    Banik, Bimal Krishna
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2018, 95 (11) : 1289 - 1294
  • [9] Sulfur-Assisted and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Catalyzed Cyclization of 2-Alkynylanilines for the Metal-Free Synthesis of Indole Derivatives
    Zhou, Hongwei
    Zhu, Da
    Xing, Yanpeng
    Huang, Huafeng
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) : 2127 - 2131
  • [10] Microwave-Assisted Facile Synthesis of Furo[3,2-b]indole Derivatives via Silver(I)-Mediated [3+2]?Cycloaddition
    Zhang, Zhiguo
    Fang, Shiliang
    Liu, Qingfeng
    Zhang, Guisheng
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (05) : 927 - 932