Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines

被引:8
|
作者
Garia, Alankrita [1 ]
Grover, Jatin [1 ]
Jain, Nidhi [1 ]
机构
[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India
关键词
Heterocyclization; Iminoiodane; Iodosyl benzene; Metal-free; Nitrene; ortho-Carbonyl anilines; N-O; 2,1-BENZISOXAZOLES ANTHRANILS; OXIDATIVE CYCLIZATION; BOND FORMATION; INHIBITORS; ACID; BENZISOXAZOLE; CONSTRUCTION; REACTIVITY; NITRILES;
D O I
10.1002/ejoc.202100756
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.
引用
收藏
页码:4125 / 4131
页数:7
相关论文
共 50 条
  • [1] PhIO Mediated One-Pot Synthesis of Pyrroloquinolinediones from ortho-Carbonyl Anilines and Maleimides
    Alahmdi, Mohammed Issa
    Mukhtar, Sayeed
    Parveen, Humaira
    Alsharif, Meshari A.
    Waheed, Mohd
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (09)
  • [2] Selectfluor™-Mediated Tandem Fluorination and 1,3-Carbonyl Migration in ortho-Carbonyl Anilines: Charge-Transfer-Enabled ortho-Selectivity
    Garia, Alankrita
    Kumar, Sharvan
    Jain, Nidhi
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (06)
  • [3] Transition Metal-Free Hydrogenolysis of Anilines to Arenes Mediated by Lithium Hydride
    Cai, Yongli
    Liu, Wei
    Yu, Yang
    Liu, Ligao
    Pei, Qijun
    Wu, Han
    He, Teng
    Guo, Jianping
    Wu, Anan
    Chen, Ping
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (38) : 17441 - 17448
  • [4] Effective metal-free electrooxidative thiocyanation of anilines
    Khodonov, Vladimir M.
    Kudinova, Anastasia S.
    Kokorekin, Vladimir A.
    Petrosyan, Vladimir A.
    Egorov, Mikhail P.
    MENDELEEV COMMUNICATIONS, 2022, 32 (01) : 94 - 96
  • [5] Synthesis of α-sulfenylated carbonyl compounds under metal-free conditions
    Mou, Dan
    Wu, Yuanyuan
    Wang, Linda
    Fu, Ying
    Du, Zhengyin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (02) : 274 - 278
  • [6] Metal-Free Intramolecular Carbonyl-Olefin Metathesis of ortho-Prenylaryl Ketones
    Soicke, Arne
    Slavov, Nikolay
    Neudoerfl, Joerg-Martin
    Schmalz, Hans-Guenther
    SYNLETT, 2011, (17) : 2487 - 2490
  • [7] PhI(OAc)2 and BF3-OEt2 mediated heterocyclization: metal-free synthesis of pyrimidine-annulated oxazolines
    Mondal, Biplab
    Hazra, Somjit
    Naktode, Kishor
    Panda, Tarun K.
    Roy, B.
    TETRAHEDRON LETTERS, 2014, 55 (41) : 5625 - 5628
  • [8] New methods in metal-free organic synthesis:: A practical procedure for carbonyl α-oxidation
    Jones, Teyrnon C.
    Tomkinson, Nicholas C. O.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [9] Transition Metal-Free Synthesis of 3-Acylquinolines through Formal [4+2] Annulation of Anthranils and Enaminones
    Zhang, Kai-Ling
    Yang, Jia-Cheng
    Guo, Qin
    Zou, Liang-Hua
    CATALYSTS, 2023, 13 (04)
  • [10] On Water: Metal-Free Synthesis of Highly Functionalized Benzothiazolylidene from ortho-Haloanilines
    Saini, Kapil Mohan
    Saunthwal, Rakesh K.
    Kumar, Shiv
    Verma, Akhilesh K.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05): : 2689 - 2698