A novel and efficient synthesis of 3,3-disubstituted indol-2-ones via Passerini three-component reactions in the presence of 4 Å molecular sieves

被引：9
|
作者：
Esmaeili, Abbas Ali [1 ,2 ]
Ghalandarabad, Saeid Amini [1 ]
Jannati, Saeideh [1 ]
机构：
[1] Univ Birjand, Fac Sci, Dept Chem, Birjand, Iran
[2] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, Mashhad, Iran
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 05期
关键词：
Isatin; Isocyanide; Passerini coupling reaction; Carboxylic acid; 3,3-Disubstituted indol-2-ones; DIALKYL ACETYLENEDICARBOXYLATES; CYANOHYDRIN ESTERS; BENZOYL CYANIDE; ALDEHYDES; ISOCYANIDES; CONVENIENT; CHEMISTRY; ISATINS; KETONES;
D O I：
10.1016/j.tetlet.2012.11.025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Passerini coupling of cyclohexylisocyanide with isatins and carboxylic acids in the presence of 4 angstrom molecular sieves is described. This process offers a highly efficient and atom-economic access to 3-acyloxy-3-carboxamido-1,3-dihydro-2H-indol-2-ones in high to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：406 / 408
页数：3
相关论文
共 50 条
  • [11] Regioselective three-component synthesis of 2,3-disubstituted quinolines via the enaminone modified Povarov reaction
    Li, Yi
    Cao, Xiaoji
    Liu, Yunyun
    Wan, Jie-Ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (45) : 9585 - 9589
  • [12] A H4 SiW12 O40 -catalyzed three-component tandem reaction for the synthesis of 3,3-disubstituted isoindolinones
    Liu, Yufeng
    Zeng, Guodong
    Cheng, Yutao
    Chen, Lei
    Liu, Yunhai
    Wei, Yongge
    Yang, Guoping
    CHINESE CHEMICAL LETTERS, 2024, 35 (01)
  • [13] A novel and green synthesis of indolone-N-amino acid derivatives via the Passerini three-component reactions in water
    Li, Rong-Kun
    Yang, Quan-Li
    Liu, Yi
    Li, Dong-Wei
    Huang, Nian-Yu
    Liu, Ming-Guo
    CHINESE CHEMICAL LETTERS, 2016, 27 (03) : 345 - 348
  • [14] A one-pot, three-component and solvent-free synthesis of 2,3-disubstituted isoindolin-1-ones
    Adib, Mehdi
    Peytam, Fariba
    Zainali, Mohsen
    Zhu, Long-Guan
    Wu, Jing
    TETRAHEDRON LETTERS, 2015, 56 (33) : 4729 - 4732
  • [15] A novel and green synthesis of indolone-N-amino acid derivatives via the Passerini three-component reactions in water
    Rong-Kun Li
    Quan-Li Yang
    Yi Liu
    Dong-Wei Li
    Nian-Yu Huang
    Ming-Guo Liu
    ChineseChemicalLetters, 2016, 27 (03) : 345 - 348
  • [16] Synthesis of 3,3-disubstituted isoindolin-1-ones via iodoamination of α-substituted secondary 2-vinylbenzamides
    Kobayashi, Kazuhiro
    Hase, Masanori
    Hashimoto, Kenichi
    Fujita, Seiki
    Tanmatsu, Miyuki
    Morikawa, Osamu
    Konishi, Hisatoshi
    SYNTHESIS-STUTTGART, 2006, (15): : 2493 - 2496
  • [17] Efficient Three-Component Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-ones in Green Media
    Kiyani, Hamzeh
    Jabbari, Morteza
    Mosallanezhad, Asiyeh
    JORDAN JOURNAL OF CHEMISTRY, 2014, 9 (04) : 279 - 288
  • [18] Zinc oxide nanoparticle promoted highly efficient one pot three-component synthesis of 2,3-disubstituted benzofurans
    Safaei-Ghomi, Javad
    Ghasemzadeh, Mohammad Ali
    ARABIAN JOURNAL OF CHEMISTRY, 2017, 10 : S1774 - S1780
  • [19] Novel and expeditious microwave-assisted three-component reactions for the synthesis of spiroimidazolin-4-ones
    Ye, P
    Sargent, K
    Stewart, E
    Liu, JF
    Yohannes, D
    Yu, LB
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08): : 3137 - 3140
  • [20] Synthesis of 2, 4-Disubstituted Quinazolines via One-Pot Three-Component Assembly
    Dasaradhan, Changalaraya
    Nawaz Khan, Fazlur-Rahman
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (06) : 3821 - 3828
12345