Synthesis of Benzothiazoles via Photooxidative Decarboxylation of α-Keto Acids

被引:50
|
作者
Monga, Aparna [1 ]
Bagchi, Sourav [1 ]
Soni, Raj Kumar [1 ]
Sharma, Anuj [1 ]
机构
[1] Indian Inst Technol Roorkee, Dept Chem, Roorkee 247667, Uttar Pradesh, India
关键词
Benzothiazoles; Blue LED; Decarboxylation; EDA complex; alpha-Keto acids; Photooxidative cross-coupling; BIOLOGICAL EVALUATION; LIGHT-IRRADIATION; N-HETEROARENES; ACYLATION; DERIVATIVES; COMPLEXES; POTENT; INHIBITORS; AMIDATION; AMINES;
D O I
10.1002/adsc.201901617
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Herein, synthesis of benzothiazoles via decarboxylative cross-coupling between alpha-keto acids and 2-aminothiophenols under blue LED irradiation without using any photocatalyst or metal at room temperature is described. The formation of benzothiazole is driven by the EDA (electron donor-acceptor) complex formed between alpha-keto acid and 2-aminothiophenol. This methodology gives easy access to 2-substituted and -unsubstituted benzothiazoles in moderate to good yields. alpha-Keto acids and 2-aminothiophenols bearing different functional groups were easily transformed under the given conditions.
引用
收藏
页码:2232 / 2237
页数:6
相关论文
共 50 条
  • [1] Synthesis of Quinazolinones and Benzothiazoles Using α-Keto Acids under Ball Milling
    Sharma, Anoop
    Singh, Jitender
    Sharma, Anuj
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (08): : 5229 - 5238
  • [2] DECARBOXYLATION OF ALPHA-KETO ACIDS
    HANSON, RW
    JOURNAL OF CHEMICAL EDUCATION, 1987, 64 (07) : 591 - 595
  • [3] α-Keto Acids as Acylating Agents in the Synthesis of 2-Substituted Benzothiazoles and Benzoselenazoles
    Lima, David B.
    Penteado, Filipe
    Vieira, Marcelo M.
    Alves, Diego
    Perin, Gelson
    Santi, Claudio
    Lenardao, Eder J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (26) : 3830 - 3836
  • [4] α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
    Huang, Jian
    Chen, Wei
    Liang, Jiazhi
    Yang, Qin
    Fan, Yan
    Chen, Mu-Wang
    Peng, Yiyuan
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 14866 - 14882
  • [5] Synthesis of β-keto sulfones via a multicomponent reaction through sulfonylation and decarboxylation
    Yu, Jiyao
    Mao, Runyu
    Wang, Qingyu
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (04): : 617 - 621
  • [6] Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters
    Huang Jiawei
    Li Xiaoman
    Xu Liang
    Wei Yu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (02) : 756 - 762
  • [7] Hydrocarbon Synthesis via Photoenzymatic Decarboxylation of Carboxylic Acids
    Zhang, Wuyuan
    Ma, Ming
    Huijbers, Mieke M. E.
    Filonenko, Georgy A.
    Pidko, Evgeny A.
    van Schie, Morten
    de Boer, Sabrina
    Burek, Bastien O.
    Bloh, Jonathan Z.
    van Berkel, Willem J. H.
    Smith, Wilson A.
    Hollmann, Frank
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (07) : 3116 - 3120
  • [8] READY DECARBOXYLATION OF IMINES OF ALPHA-KETO ACIDS - MECHANISM AND APPLICATION TO THIOAMIDE SYNTHESIS
    ALY, MF
    GRIGG, R
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (21) : 1523 - 1524
  • [9] ON THE MECHANISM OF OXIDATIVE DECARBOXYLATION OF ALPHA-KETO ACIDS
    SANADI, DR
    LANGLEY, M
    WHITE, F
    BIOCHIMICA ET BIOPHYSICA ACTA, 1958, 29 (01) : 218 - 219
  • [10] SPECTROPHOTOMETRIC STUDIES ON THE DECARBOXYLATION OF BETA-KETO ACIDS
    KORNBERG, A
    OCHOA, S
    MEHLER, AH
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1948, 174 (01) : 159 - 172