Visible-Light-Induced Decarboxylative Annulation of α,β-Unsaturated Acids with Amines and α-Keto Acids for 2,4-Diarylquinoline Synthesis

被引:0
|
作者
Das, Suman [1 ]
Maiti, Souvik [1 ]
Mondal, Soumya [1 ]
Mondal, Subal [1 ]
Midya, Siba P. [2 ]
Ghosh, Pradyut [1 ]
机构
[1] Indian Assoc Cultivat Sci, Sch Chem Sci, Kolkata 700032, West Bengal, India
[2] Rammohan Coll, Dept Chem, Kolkata 700009, West Bengal, India
关键词
CARBOXYLIC-ACIDS; PHOTOREDOX CATALYSIS; 2-SUBSTITUTED QUINOLINES; REGIOSELECTIVE SYNTHESIS; CINNAMIC-ACIDS; METAL; ACCESS; CYCLIZATION; 2-ETHYNYLANILINES; PYRIDINES;
D O I
10.1021/acs.orglett.5c00099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and sustainable approach for the synthesis of 2,4-diarylquinolines has been developed via a visible-light-promoted metal-free three-component decarboxylative annulation pathway. This one-pot protocol combines readily available feed-stock alpha,beta-unsaturated acids, aromatic amines, and alpha-keto acids in a cascade manner to access substituted quinolines under eco-benign conditions. Moreover, mechanistic insights suggest initial C-C cross coupling followed by decarboxylative 6 pi electrocyclic annulation to afford the desired products. The broad substrates scope and excellent functional group tolerance make this protocol more attractive and synthetically applicable toward the construction of complex N-heterocycles.
引用
收藏
页码:1537 / 1543
页数:7
相关论文
共 50 条
  • [1] Visible-Light-Induced Decarboxylative Functionalization of Carboxylic Acids and Their Derivatives
    Xuan, Jun
    Zhang, Zhao-Guo
    Xiao, Wen-Jing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (52) : 15632 - 15641
  • [2] Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
    Jiang, Min
    Yang, Haijun
    Jin, Yunhe
    Ou, Lunyu
    Fu, Hua
    SYNLETT, 2018, 29 (12) : 1572 - 1577
  • [3] Visible-light-induced decarboxylative annulation of silanecarboxylic acids with 2-isocyanobiaryls to 6-silyl-substituted phenanthridines
    Deng, Cailin
    Zhang, Tiankai
    Tian, Ye
    Gao, Pan
    Zhang, Guodong
    Chen, Feng
    MOLECULAR CATALYSIS, 2024, 560
  • [4] Visible-light-induced decarboxylative alkynylation of carboxylic acids in batch and continuous flow
    Qin, Longzhou
    Zhang, Xinpeng
    Sun, Hao
    Duan, Xiu
    Liu, Jie
    Wu, Mengyu
    Yuan, Xin
    Qiu, Jiangkai
    Guo, Kai
    GREEN SYNTHESIS AND CATALYSIS, 2024, 5 (01): : 20 - 24
  • [5] Visible-Light-Induced Decarboxylative Fluorination of Aliphatic Carboxylic Acids Catalyzed by Iron
    Zhang, Yu
    Qian, Jiahui
    Wang, Miao
    Huang, Yahao
    Hu, Peng
    ORGANIC LETTERS, 2022, 24 (32) : 5972 - 5976
  • [6] Visible-Light-Induced Metal-Free Decarboxylative Perfluoroalkylation of Aryl Acrylic Acids
    Yu, Mo
    Niu, Kaikai
    Wang, Ziwen
    Liu, Yuxiu
    Wang, Qingmin
    ORGANIC LETTERS, 2022, 24 (41) : 7622 - 7626
  • [7] Visible-Light-Induced Decarboxylative Cyclization of 2-Alkenylarylisocyanides with α-Oxocarboxylic Acids: Access to 2-Acylindoles
    Zhang, Xiaofei
    Zhu, Peiyuan
    Zhang, Ruihong
    Li, Xiang
    Yao, Tuanli
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15): : 9503 - 9513
  • [8] Visible-Light-Induced Synthesis of Vinyl Sulfones via Decarboxylative Sulfonylation of Cinnamic Acids Using Sulfonylazides/p-Toluenesulfonylmethyl Isocyanide/β-Keto Sulfones
    Ishu, Km
    Kumar, Mahesh
    Singh, Krishna Nand
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (15): : 10919 - 10928
  • [9] Photosensitizer-free synthesis of β-keto sulfones via visible-light-induced oxysulfonylation of alkenes with sulfonic acids
    Peng, Zhen
    Hong, Yun-Yun
    Peng, Sha
    Xu, Xiang-Qun
    Tang, Shan-Shan
    Yang, Li-Hua
    Xie, Long-Yong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (20) : 4537 - 4541
  • [10] Synthesis of Diverse Oxetane Amino Acids via Visible-Light-Induced Photocatalytic Decarboxylative Giese-Type Reaction
    Shi, Haoliang
    Wan, Yi
    Zhang, Yongqiang
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (12) : 1341 - 1346