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
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
  • [41] 2-(1H-Imidazol-2-yl)-2,3-dihydro-1H-perimidine
    Petkova, Zhanina
    Rusew, Rusi
    Bakalova, Snezhana
    Shivachev, Boris
    Kurteva, Vanya
    MOLBANK, 2023, 2023 (01)
  • [42] Potassium [1-(tert-Butoxycarbonyl)-1H-indol-2-yl]trifluoroborate as an Efficient Building Block in Palladium-Catalyzed Suzuki-Miyaura Cross Couplings
    Kassis, Pamela
    Beneteau, Valerie
    Merour, Jean-Yves
    Routier, Sylvan
    SYNTHESIS-STUTTGART, 2009, (14): : 2447 - 2453
  • [43] Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes
    Zhang, Yan
    Guo, Dongmei
    Ye, Shangyi
    Liu, Zhicheng
    Zhu, Gangguo
    ORGANIC LETTERS, 2017, 19 (06) : 1302 - 1305
  • [44] Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines
    Ye, Yibin
    Cheung, Kelvin Pak Shing
    He, Lisi
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2018, 20 (06) : 1676 - 1679
  • [45] Design and synthesis of novel 2-(indol-5-yl)thiazole derivatives as xanthine oxidase inhibitors
    Song, Jeong Uk
    Choi, Sung Pil
    Kim, Tae Hun
    Jung, Cheol-Kyu
    Lee, Joo-Youn
    Jung, Sang-Hun
    Kim, Geun Tae
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (06) : 1254 - 1258
  • [46] Synthesis and in vitro antifungal evaluation of 2-(2,4-difluorophenyl)-1-[(1H-indol-3-ylmethyl)methylamino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ols
    Guillon, Remi
    Loge, Cedric
    Pagniez, Fabrice
    Ferchaud-Roucher, Veronique
    Duflos, Muriel
    Picot, Carine
    Le Pape, Patrice
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2011, 26 (02) : 261 - 269
  • [47] ONE-POT FOUR COMPONENT REACTION FOR THE SYNTHESIS OF 1-(1H-INDOL-2-YL)-1H-PYRAZOLO [1,2-b]PHTHALAZINE-5,10-DIONE DERIVATIVES BY SELF-CATALYSIS
    Mohammad, Faruq
    Al-Lohedan, Hamad A.
    HETEROCYCLES, 2017, 94 (08) : 1567 - 1572
  • [48] Multicomponent Cascade Reaction of 3-Cyanochromones: Highly Site-Selective Synthesis of 2-(1H-Imidazol-1-yl)-4H-chromen-4-one Derivatives
    Lv, Ying
    Chen, Li
    Li, Kun
    Yun, Xing-Han
    Yan, Sheng-Jiao
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22) : 15187 - 15196
  • [49] Synthesis of 2-(Indol-3-yl)-ethanone-based Arylhydrocarbon Receptor Agonist Candidates via Weinreb Amides of Indole-3-acetic Acid
    Opietnik, Martina
    Jungbauer, Alois
    Mereiter, Kurt
    Rosenau, Thomas
    CURRENT ORGANIC SYNTHESIS, 2013, 10 (05) : 812 - 818
  • [50] Synthesis of β-D-glucopyranosides of 6-substituted 2-(indol-3-yl)benzothiazoles
    Humeník, M
    Kutschy, P
    Valková, K
    Horváth, B
    Kovácik, V
    Bekesová, S
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2005, 70 (01) : 72 - 84