Ascorbic acid: an efficient organocatalyst for environmentally benign synthesis of indole-substituted 4H-chromenes

被引:9
|
作者
Das, Debjit [1 ]
机构
[1] Triveni Devi Bhalotia Coll, Dept Chem, Raniganj, India
来源
MONATSHEFTE FUR CHEMIE | 2021年 / 152卷 / 08期
关键词
2-Amino-4H-chromene; Organocatalyst; Ascorbic acid; Green synthesis; Indole; Multicomponent reaction; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; 3-SUBSTITUTED INDOLES; CATALYST; GREEN; NANOCOMPOSITE;
D O I
10.1007/s00706-021-02824-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An expedient, straightforward, and efficient one-pot three-component synthesis of biologically relevant indole-substituted 4H-chromenes has been developed by the reaction of various indoles, malononitrile, and salicylaldehydes using a catalytic amount of ascorbic acid in aqueous ethanol at room temperature. The significant features of the developed protocol are the clean reaction profile, operational simplicity, non-hazardous experimental conditions, no column chromatographic purification, use of an inexpensive, commercially available, and non-toxic metal-free catalyst, accomplishment of good to excellent yields, and large-scale synthesis.
引用
收藏
页码:987 / 991
页数:5
相关论文
共 50 条
  • [41] Synthesis of 4H-chromenes promoted by NbCl5 through multicomponent reaction
    Oshiro, Paula Beatriz
    da Silva Gomes Lima, Paula Souza
    de Menezes, Manoel Lima
    da Silva-Filho, Luiz Carlos
    [J]. TETRAHEDRON LETTERS, 2015, 56 (30) : 4476 - 4479
  • [42] Multicomponent assembly of 2-amino-4-substituted 4H-chromenes using cyclic Michael donors
    Lakshmi, Neelakandan Vidhya
    Kiruthika, Selvarangam E.
    Perumal, P. T.
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2013, 91 (06) : 479 - 485
  • [43] Enantioselective Synthesis of Chromanes by Iridium-Catalyzed Asymmetric Hydrogenation of 4H-Chromenes
    Valla, Carine
    Baeza, ALejandro
    Menges, Frederik
    Pfaltz, Andreas
    [J]. SYNLETT, 2008, (20) : 3167 - 3171
  • [44] Gold(III)-Catalyzed Tandem Reaction of Ketones with Phenols: Efficient and Highly Selective Synthesis of Functionalized 4H-Chromenes
    Liu, Yunkui
    Qian, Jianqiang
    Lou, Shaojie
    Zhu, Jie
    Xu, Zhenyuan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (04): : 1309 - 1312
  • [45] Recyclization of carbonyl-substituted 4H-chromenes and 1H-benzo[f]chromenes by the action of amidines and guanidine: a novel method for the synthesis of ortho-hydroxybenzylpyrimidines
    Yulia V. Popova
    Darina V. Sakhnenko
    Irina V. Arbuzova
    Vitaly A. Osyanin
    Dmitry V. Osipov
    Yuri N. Klimochkin
    [J]. Chemistry of Heterocyclic Compounds, 2016, 52 : 803 - 808
  • [46] Recyclization of carbonyl-substituted 4H-chromenes and 1H-benzo[f]chromenes by the action of amidines and guanidine: a novel method for the synthesis of ortho-hydroxybenzylpyrimidines
    Popova, Yulia V.
    Sakhnenko, Darina V.
    Arbuzova, Irina V.
    Osyanin, Vitaly A.
    Osipov, Dmitry V.
    Klimochkin, Yuri N.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (10) : 803 - 808
  • [47] Efficient Synthesis of Functionalized 4H-Chromenes via an Fe(OTf)3-Catalyzed Cyclization Reaction of Phenols and Ketones
    Deng, Kai
    Huai, Qi-Yong
    Li, Hui-Jing
    Wang, Jun-Hu
    Yang, Hui-Ru
    Liu, Ying
    Wu, Yan-Chao
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (07): : 1482 - 1492
  • [48] A simple Lewis acid induced reaction of phenols with electrophiles: Synthesis of functionalized 4H-chromenes and ortho-benzylphenols
    Sreenivasulu, Chinnabattigalla
    Thadathil, Ditto Abraham
    Pal, Sumit
    Gedu, Satyanarayana
    [J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (01) : 112 - 122
  • [49] Alkylaminopyridine-grafted on HY Zeolite: Preparation, characterization and application in synthesis of 4H-Chromenes
    Zendehdel, Mojgan
    Bodaghifard, Mohammad Ali
    Behyar, Hakimeh
    Mortezaei, Zohreh
    [J]. MICROPOROUS AND MESOPOROUS MATERIALS, 2018, 266 : 83 - 89
  • [50] An Efficient ZnO-Nanoparticle-Catalyzed Regio- and Chemoselective Synthesis of Novel Functionalized 4H-Chromenes in Aqueous Medium
    Rao, Lenka Chandrasekhara
    Kumar, Nandigama Satish
    Bheeram, Vema Reddy
    Hemambika, Sadasivuni
    Mukkamala, Sarathchandra Babu
    [J]. CHEMISTRYSELECT, 2018, 3 (26): : 7485 - 7489