Microwave-Assisted Regioselective Friedel-Crafts Arylation by BF3 . OEt2: A Facile Synthetic Access to 3-Substituted-3-Propargyl Oxindole Scaffolds

被引：11
|
作者：
Laxmikeshav, Kritika [1 ]
Sakla, Akash P. [1 ]
Rasane, Sai [1 ]
John, Stephy Elza [1 ]
Shankaraiah, Nagula [1 ]
机构：
[1] Natl Inst Pharmaceut Educ & Res NIPER, Dept Med Chem, Hyderabad 500037, Telangana, India
来源：
CHEMISTRYSELECT | 2020年 / 5卷 / 23期
关键词：
C-C bond formation; 3; 3-disubstituted oxindole; Friedel-Crafts arylation; Lewis acids; Microwave Chemistry; AROMATIC-COMPOUNDS; ORGANIC-SYNTHESIS; TERMINAL ALKYNES; ALLYLIC ALCOHOLS; GREEN SYNTHESIS; ANTI-HIV; PROPARGYLATION; SUBSTITUTION; DESIGN; CYCLOADDITION;
D O I：
10.1002/slct.202001660
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile microwave-assisted synthetic strategy for the construction of C-C bondviaregioselective Friedel-Crafts arylation of 3-hydroxy-3-phenylethynyl oxindoles with different electron-rich nucleophiles such as phenols, sulphonamides, anisole, benzofuran, and benzothiophene has been established by employing BF3 . OEt(2)as catalyst. The current protocol attributes mild conditions, cost-effective, transition-metal free synthesis, wide substrate scope and moderate to good yields. Moreover, this method is amenable for the generation of a library of densely substituted 3-(4-hydroxyphenyl)-3-(phenylethynyl) oxindoles and 3-(4-benzenesulphonamide)-3-(phenylethynyl) oxindoles as privileged scaffolds.
引用
收藏
页码：7004 / 7012
页数：9
相关论文
共 47 条
  • [31] Ga(OTf)3-Catalyzed Temperature-Controlled Regioselective Friedel-Crafts Alkylation of Trifluoromethylated 3-Indolylmethanols with 2-Substituted Indoles: Divergent Synthesis of Trifluoromethylated Unsymmetrical 3,3′-and 3,6′-Bis(indolyl)methanes
    Ling, Yuan
    An, Di
    Zhou, Yuanyuan
    Rao, Weidong
    ORGANIC LETTERS, 2019, 21 (09) : 3396 - 3401
  • [32] The rapid construction and biological evaluation of densely substituted pyrrolo[1,2-a]indoles via a BF3<middle dot>OEt2-assisted cascade approach
    Mali, Ghanshyam
    Yadav, Vinay Kumar
    Priya, Himani
    Shukla, Manjari
    Pandey, Peeyush
    Kumar, Akhilesh
    Paranjothy, Manikandan
    Bhattacharyya, Sudipta
    Erande, Rohan D.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (48) : 9659 - 9668
  • [33] Chiral Bronsted acid catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated ketones: short access to optically active 2-and 3-substituted indole derivatives
    Sakamoto, Tsubasa
    Itoh, Junji
    Mori, Keiji
    Akiyama, Takahiko
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (23) : 5448 - 5454
  • [34] A microwave-assisted, facile, regioselective Friedlander synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2-b]quinolines
    Balamurugan, Kamaraj
    Jeyachandran, Veerappan
    Perumal, Subbu
    Manjashetty, Thimmappa H.
    Yogeeswari, Perumal
    Sriram, Dharmarajan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) : 682 - 688
  • [35] Microwave-assisted synthesis of β-amino-α,β-unsaturated esters: a rapid and efficient access to (Z)-methyl 3-amino-2-substituted acrylate
    Cao, Han
    Liu, Xue-jing
    Li, Peng-fei
    Bie, Fu-sheng
    Shi, Yi-jun
    Yan, Peng
    Han, Ying
    SYNTHETIC COMMUNICATIONS, 2021, 51 (14) : 2160 - 2167
  • [36] AlCl3-mediated tandem Friedel-Crafts reactions of vinylidenecyclopropanes with acyl chlorides:: a facile synthetic method for the construction of 1-[2-(2,2-diarylvinyl)-1-phenyl-3H-inden-5-yl]ethanone derivatives
    Shi, Min
    Wu, Lei
    Lu, Jian-Mei
    TETRAHEDRON, 2008, 64 (15) : 3315 - 3321
  • [37] Pyridine-based, microwave-assisted one-pot synthetic protocol for the synthesis of ethyl 3-substituted-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates
    Sourabh Mundra
    Radhakrishnan Mahesh
    Research on Chemical Intermediates, 2016, 42 : 4207 - 4219
  • [38] Pyridine-based, microwave-assisted one-pot synthetic protocol for the synthesis of ethyl 3-substituted-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates
    Mundra, Sourabh
    Mahesh, Radhakrishnan
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (05) : 4207 - 4219
  • [39] Microwave-assisted Rhodium(I)-Catalyzed C8-Regioselective C-H Alkenylation and Arylation of 1,2,3,4-Tetrahydroquinolines with Alkenyl and Aryl Carboxylic Acids
    Zhao, Haoqiang
    Zeng, Qi
    Yang, Ji
    Huang, Xinran
    Li, Xiaohan
    Lei, Haimin
    Xu, Lijin
    Walsh, Patrick J.
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (08) : 1820 - 1826
  • [40] A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles
    Karthikeyan, Subramanian Vedhanarayanan
    Perumal, Subbu
    Shetty, Krithika Arun
    Yogeeswari, Perumal
    Sriram, Dharmarajan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (11) : 3006 - 3009
12345