Synthesis of 2-(1H-Indol-2-yl)acetamides via Bronsted Acid-Assisted Cyclization Cascade

被引:15
|
作者
Aksenov, Nicolai A. [1 ]
Aksenov, Dmitrii A. [1 ]
Skomorokhov, Anton A. [1 ]
Prityko, Lidiya A. [1 ]
Aksenov, Alexander V. [1 ]
Griaznov, Georgii D. [2 ]
Rubin, Michael [1 ,2 ]
机构
[1] North Caucasus Fed Univ, Dept Chem, Stavropol 355009, Russia
[2] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 19期
基金
俄罗斯科学基金会;
关键词
INHIBITORY-ACTIVITY; MICHAEL ADDITION; HISTONE; 2'-AMINOCHALCONES; NITROSTYRENES; REDUCTION; DISCOVERY; EFFICIENT; INDOLES; ROUTE;
D O I
10.1021/acs.joc.0c01344
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and straightforward Bronsted-acid mediated cascade process was developed, involving cyclization of readily available beta-ketonitriles into 2-aminofurans, and their subsequent recyclization into 2-(1H-indol-2-yl)acetamides is developed. This synthetic route opens a new avenue for an expeditious assembly of
引用
收藏
页码:12128 / 12146
页数:19
相关论文
共 50 条
  • [31] Dichloridobis(2-{1-[2-(1H-indol-3-yl)-ethyliminio]ethyl}phenolate-κO)zinc(II)-2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}-phenolate (1/2)
    Ali, Hapipah M.
    Ibrahim, Mohamed
    Mustafa, Mohamed
    Rizal, Mohd. Razali
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : M718 - U923
  • [32] Discovery of N-(1-Acryloylazetidin-3-yl)-2-(1H-indol-1-yl)acetamides as Covalent Inhibitors of KRASG12C
    Shin, Youngsook
    Jeong, Joon Won
    Wurz, Ryan P.
    Achanta, Pragathi
    Arvedson, Tara
    Bartberger, Michael D.
    Campuzano, Iain D. G.
    Fucini, Ray
    Hansen, Stig K.
    Ingersoll, John
    Iwig, Jeffrey S.
    Lipford, J. Russell
    Ma, Vu
    Kopecky, David J.
    McCarter, John
    San Miguel, Tisha
    Mohr, Christopher
    Sabet, Sudi
    Saiki, Anne Y.
    Sawayama, Andrew
    Sethofer, Steven
    Tegley, Christopher M.
    Volak, Laurie P.
    Yang, Kevin
    Lanman, Brian A.
    Erlanson, Daniel A.
    Cee, Victor J.
    ACS MEDICINAL CHEMISTRY LETTERS, 2019, 10 (09): : 1302 - 1308
  • [33] One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
    Xie, Jialin
    Guo, Zhonglin
    Huang, Yuanqiong
    Qu, Yi
    Song, Hongjian
    Song, Haibin
    Liu, Yuxiu
    Wang, Qingmin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 490 - 495
  • [34] Synthesis of N-substituted derivatives of 2-(5-amino-2-methyl-1H-indol-3-yl)acetic acid
    Maklakov, SA
    Smushkevich, YI
    Magedov, IV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (05): : 619 - 622
  • [35] Synthesis of substituted 1H-indol-2-yl-1H-quinolin-2-ones.
    Kuethe, JT
    Wong, A
    Smitrovich, J
    Qu, CX
    Davies, IW
    Dormer, PG
    Hughes, DL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U158 - U158
  • [36] 2′-[(5-bromo-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide ethyl acetate solvate
    Ali, Hapipah M.
    Shimar, Jamaludin Nazzatush
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O2731 - U1620
  • [37] Calorimetric and computational study of (1H-Indol-n-yl)methanol and 2-(1H-Indol-n-yl)ethanol (n=2, 3)
    Carvalho, Tania M. T.
    Amaral, Luisa M. P. F.
    Morais, Victor M. F.
    Ribeiro da Silva, Maria D. M. C.
    THERMOCHIMICA ACTA, 2019, 673 : 169 - 176
  • [38] N-(2-(1H-Indol-3-yl)ethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
    Manolov, Stanimir
    Ivanov, Iliyan
    Bojilov, Dimitar
    MOLBANK, 2021, 2021 (01) : 1 - 4
  • [39] Novel inhibitors of epidermal growth factor receptor: (4-(Arylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(1H-indol-2-yl)methanones and (1H-indol-2-yl)(4-(phenylamino)thieno[2,3-d]pyrimidin-6-yl)methanones
    Beckers, Thomas
    Sellmer, Andreas
    Eichhorn, Emerich
    Pongratz, Herwig
    Schaechtele, Christoph
    Totzke, Frank
    Kelter, Gerhard
    Krumbach, Rebekka
    Fiebig, Heinz-Herbert
    Boehmer, Frank-D.
    Mahboobi, Siavosh
    BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (01) : 125 - 136
  • [40] The effect of hydrogen bonding on the conformations of 2-(1H-indol-3-yl)-2-oxoacetamide and 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
    Sonar, Vijayakumar N.
    Parkin, Sean
    Crooks, Peter A.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2012, 68 : O405 - U226