Convenient synthesis of 3-unsubstituted oxindole-1-carboxamides

被引：0
|
作者：
Porcs-Makkay, Marta [1 ]
Volk, Balazs [1 ]
Kokai, Eszter [2 ]
Simig, Gyula [1 ]
机构：
[1] EGIS Pharmaceut Plc, Div Chem Res, H-1475 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Fac Chem Engn, H-1521 Budapest, Hungary
来源：
TETRAHEDRON | 2012年 / 68卷 / 05期
关键词：
Oxindole; Amidation; Dephenoxycarbonylation; 4-N; N-Dimethylaminopyridinum; (DMAP); salt; DERIVATIVES;
D O I：
10.1016/j.tet.2011.12.027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The multiple reactivity of the mesomeric anion formed by N- or C(3)-deprotonation of 3-unsubstituted oxindoles hampers the selective introduction of substituents onto the nitrogen atom. A conveniently applicable reaction sequence has been elaborated for the synthesis of 3-unsubstituted oxindole-1-carboxamides starting from the easily available 1,3-bis(phenoxycarbonyl)oxindoles. Selective amidation of the N-phenoxycarbonyl moiety and subsequent removal of the C(3)-phenoxycarbonyl moiety furnished the title compounds, which are useful building blocks for further functionalization. Besides the novel methodologies, several new representatives of this valuable compound family and their intermediates are also described below. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1427 / 1435
页数：9
相关论文
共 50 条
  • [21] Synthesis and biological activity of new pyranochromen-3-carboxamides
    Shutov, R. V.
    Kuklina, E. V.
    Anisimova, N. A.
    Anan'ev, E. P.
    Kotova, N. I.
    Kuklin, V. N.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2012, 46 (01) : 10 - 14
  • [22] Diversity-Oriented Synthesis of 1-Substituted 4-Aryl-6-oxo-1,6-dihydropyridine-3-carboxamides
    Baskovc, Jernej
    Dahmann, Georg
    Golobic, Amalija
    Groselj, Uros
    Kocar, Drago
    Stanovnik, Branko
    Svete, Jurij
    ACS COMBINATORIAL SCIENCE, 2012, 14 (09) : 513 - 519
  • [23] Access to 2,3-Unsubstituted Imidazo[2,1-b][1,3]benzothiazole Using Ethylene Glycol as a C2 Precursor and Subsequent Regioselective C3 Functionalization
    Maity, Sujit
    Panda, Niranjan
    CHEMISTRYSELECT, 2024, 9 (12):
  • [24] A convenient synthesis of indoloquinolinones via 3-arylation of indole-2-carboxamides and PIDA-mediated C-N bond formation
    Li, Yulin
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    TETRAHEDRON, 2015, 71 (19) : 2927 - 2935
  • [25] Synthesis of Pyrrolo(spiro-[2.3′]-oxindole)-spiro-[4.3"]-oxindole via 1,3-Dipolar Cycloaddition of Azomethine Ylides with 3-Acetonylideneoxindole
    Xiao, Jun-An
    Zhang, Hong-Gang
    Liang, Shan
    Ren, Ji-Wei
    Yang, Hua
    Chen, Xiao-Qing
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22): : 11577 - 11583
  • [26] Synthesis of substituted 3-amino-N-phenyl-1H-indazole-1-carboxamides endowed with antiproliferative activity
    Maggio, Benedetta
    Raimondi, Maria Valeria
    Raffa, Demetrio
    Plescia, Fabiana
    Cascioferro, Stella
    Plescia, Salvatore
    Tolomeo, Manlio
    Di Cristina, Antonietta
    Pipitone, Rosaria Maria
    Grimaudo, Stefania
    Daidone, Giuseppe
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) : 168 - 174
  • [27] Parallel synthesis of 7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamides
    Ahmetaj, Sizana
    Velikanje, Nina
    Groselj, Uros
    Sterbal, Ines
    Prek, Benjamin
    Golobic, Amalija
    Kocar, Drago
    Dahmann, Georg
    Stanovnik, Branko
    Svete, Jurij
    MOLECULAR DIVERSITY, 2013, 17 (04) : 731 - 743
  • [28] Design, Synthesis and Cytotoxic Activity of Spiro(oxindole-3-3'-pyrrolidine) Derivatives
    Konyar, Dilan
    Andac, Cenk A.
    Buyukbingol, Erdem
    LETTERS IN DRUG DESIGN & DISCOVERY, 2018, 15 (01) : 37 - 45
  • [29] A Convenient Route for the Synthesis of 3-Deazaspongosine
    Bande, Omprakash
    Herdewijn, Piet
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (01) : 231 - 236
  • [30] Convenient Synthesis of 3-Glycosylated Isocoumarins
    Sudarshan, Kasireddy
    Aidhen, Indrapal Singh
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (01) : 34 - 38
12345