3-Chlorophenylboronic acid-promoted, one-pot, aza-Friedel-Crafts reaction of indoles

被引:3
作者
Goswami, Santosh V. [1 ]
Thorat, Prashant B. [1 ]
Shukla, Mahesh V. [1 ]
Bhusare, Sudhakar R. [1 ]
机构
[1] Dnyanopasak Coll, Dept Chem, Parbhani 431401, Maharashtra, India
关键词
Aza-Friedel-Crafts reaction; 3-Chlorophenylboronic acid; Indole; Aromatic aldehyde; N; N-Dimethylaniline; PHENYLBORONIC ACID; EFFICIENT; OPTIMIZATION; CATALYST; TANDEM; WATER; MILD;
D O I
10.1007/s11164-013-1370-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3-Chlorophenylboronic acid promotes efficient synthesis of 3-substituted indole derivatives via aza-Friedel-Crafts reaction of indoles, aromatic aldehydes, and N,N-dimethylaniline at room temperature. The mild reaction conditions, excellent yields, and easy experimental workup are striking features of this procedure for synthesis of 3-substituted indoles.
引用
收藏
页码:2583 / 2589
页数:7
相关论文
共 50 条
  • [21] Lithium Chloride-Promoted Brønsted Acid-Catalyzed Friedel-Crafts Alkylation Reaction of Indoles with Aldehydes and Ketones "on Water"
    Yang, Jun
    Zhang, Jianyu
    Li, Tianxing
    Liu, Yunting
    Jin, Hui
    Ryu, Do Hyun
    Zhang, Lixin
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [22] Acetic acid-promoted, efficient, one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones
    Karimi-Jaberi, Zahed
    Arjmandi, Reza
    MONATSHEFTE FUR CHEMIE, 2011, 142 (06): : 631 - 635
  • [23] Supported Bifunctional Chiral Thioureas as Catalysts in the Synthesis of 3-Amino-2-Oxindoles through Enantioselective aza-Friedel-Crafts Reaction: Application in Continuous Flow Processes
    Rodriguez-Rodriguez, Marta
    Maestro, Alicia
    Andres, Jose M.
    Pedrosa, Rafael
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (13) : 2744 - 2754
  • [24] Lewis-Acid-Catalyzed Intramolecular Aza-Friedel-Crafts Reaction of N-tert-Butanesulfinyl Imines: Efficient Synthesis of Optically Active 9-Aminofluorene Derivatives
    Li, Yi
    Xu, Ming-Hua
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (01) : 50 - 53
  • [25] Biopolymeric alginic acid: an efficient recyclable green catalyst for the Friedel-Crafts reaction of indoles with isoquinoline-1,3,4-triones in water
    Srivastava, Anvita
    Yadav, Anubha
    Samanta, Sampak
    TETRAHEDRON LETTERS, 2015, 56 (44) : 6003 - 6007
  • [26] Preparation of Bicyclic Ketal Skeletons with Aldehyde and α-Ketone Acid through Cascade Friedel-Crafts Reaction and Stereoselective Acetalization in One Pot
    Li, Ling
    Wang, Ying-wei
    Zhang, Shi-qi
    Dong, Xiong-fei
    Li, Guang-xun
    Zhao, Gang
    Tang, Zhuo
    SYNLETT, 2019, 30 (18) : 2091 - 2095
  • [27] One-pot solvent-free synthesis of triaryl- and triheteroarylmethanes by Bi(OTf)3-catalyzed Friedel-Crafts reaction of arenes/heteroarenes with trialkyl orthoformates
    Tuengpanya, Surisa
    Chantana, Chayamon
    Sirion, Uthaiwan
    Siritanyong, Wipada
    Srisook, Klaokwan
    Jaratjaroonphong, Jaray
    TETRAHEDRON, 2018, 74 (33) : 4373 - 4380
  • [28] Acetic acid-promoted eco-friendly one-pot pseudo six-component synthesis of bis-spiro-substituted piperidines
    Mousavi, Mir Rasul
    Gharari, Hadigheh
    Maghsoodlou, Malek Taher
    Hazeri, Nourallah
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (04) : 3875 - 3886
  • [29] Catalyst-free, ethylene glycol promoted one-pot three component synthesis of 3-amino alkylated indoles via Mannich-type reaction
    Rajesh, U. Chinna
    Kholiya, Rohit
    Pavan, V. Satya
    Rawat, Diwan S.
    TETRAHEDRON LETTERS, 2014, 55 (18) : 2977 - 2981
  • [30] Base-Promoted Three-Component One-Pot Synthesis of 3-(Thiomethyl)indoles with Paraformaldehyde under Aqueous Conditions
    Xiao, Fuhong
    Yuan, Shanshan
    Huang, Huawen
    Deng, Guo-Jun
    SYNLETT, 2018, 29 (20) : 2693 - 2696