Synthesis of (4-nitro-1H-indol-6-yl)- and (4-amino-1H-indol-6-yl)phosphonic acid derivatives

被引：0
|
作者：
Aleksandr A. Shalimov
Mykola V. Kolotylo
Lyubov V. Babiy
Oksana V. Muzychka
Petro P. Onys’ko
Vladimir V. Rozhkov
机构：
[1] Institute of Organic Chemistry,
[2] National Academy of Sciences of Ukraine,undefined
[3] I. F. Lab. Ltd.,undefined
来源：
Chemistry of Heterocyclic Compounds | 2018年 / 54卷
关键词：
4-aminoindole; enamine; (1; -indol-6-yl)phosphonate; (4-methyl-3,5-dinitrophenyl)phosphonic acid; 4-nitroindole; Batcho–Leimgruber indole synthesis;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A convenient methodology for the synthesis of previously unreported (1H-indol-6-yl)phosphonic acid derivatives has been described. Reaction of (4-methyl-3,5-dinitrophenyl)phosphonates with dimethylformamide dimethyl acetal leads to the respective enamines that can be readily converted into indoles by the Batcho–Leimgruber synthetic protocol. Proper choice of reducing agent for the reductive cyclization of intermediate enamines allows to selectively obtain (4-nitro-1H-indol-6-yl)- and (4-amino-1H-indol-6-yl)phosphonates.
引用
收藏
页码：1033 / 1039
页数：6
相关论文
共 50 条
  • [21] 4-Amino-5-benzoyl-1-benzyl-2-(4,5,6,7-tetrahydro-1H-indol-2- yl)-1H-pyrrole-3-carbonitrile
    Petrova, Olga V.
    Ushakov, Igor A.
    Sobenina, Lyubov N.
    Kireeva, Victoriya V.
    Trofimov, Boris A.
    MOLBANK, 2023, 2023 (01)
  • [22] Synthesis of 4,6-disubstituted-2-(1H-indol-3-yl)-benzothiazoles
    Záletová, J
    Dzurilla, M
    Kutschy, P
    Pazdera, P
    Kovácik, V
    Aldölfi, J
    Bekesová, S
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2004, 69 (02) : 453 - 460
  • [23] Synthesis of N-substituted derivatives of (5-amino-2-methyl-1H-indol-3-YL)acetic acid
    Maklakov S.A.
    Smushkevich Yu.I.
    Magedov I.V.
    Chemistry of Heterocyclic Compounds, 2002, 38 (5) : 539 - 542
  • [24] The synthesis of 2-(indol-1-yl)propionic acid derivatives
    Kurkin, AV
    Golantsov, NE
    Karchava, AV
    Yurovskaya, MA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2003, (01): : 78 - 86
  • [25] 4-INDOL-3-YL-1-METHYLHEXAHYDROAZEPINES
    HESTER, JB
    JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12): : 4098 - &
  • [26] 2′-[(5-chloro-1H-indol-3-yl)methylene]2-(1H-indol-3-yl)acetohydrazide
    Ali, Hapipah M.
    Shimar, Jamaludin Nazzatush
    Jefrey, Basirun Wan
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O1807 - O1808
  • [27] An improved synthesis of 1-acetyl-1H-indol-3-yl acetates
    Rodriguez-Dominguez, Juan C.
    Balbuzano-Deus, Alexander
    Lopez-Lopez, Miguel A.
    Kirsch, Gilbert
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (01) : 273 - 275
  • [28] Synthesis of novel 2-amino-4-(5′-substituted 2′-phenyl-1H-indol-3′-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents
    Saundane, Anand R.
    Vijaykumar, Katkar
    Vaijinath, A. Verma
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (07) : 1978 - 1984
  • [29] 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
  • [30] 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
12345