Transition-Metal-Free Tandem Oxidative Removal of Benzylic Methylene Group by C-C and C-N Bond Cleavage Followed by Intramolecular New Aryl C-N Bond Formation under Radical Conditions

被引：43
|
作者：
Laha, Joydev K. [1 ]
Tummalapalli, K. S. Satyanarayana [1 ]
Gupta, Ankur [1 ]
机构：
[1] Natl Inst Pharmaceut Educ & Res, Dept Pharmaceut Technol Proc Chem, Sas Nagar 160062, Punjab, India
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 17期
关键词：
CARBON-NITROGEN BOND; ALIPHATIC CARBOXYLIC-ACIDS; SECONDARY-AMINES; 2-ARYL BENZOTHIAZOLES; KETONES; AMIDES; TRANSFORMATION; CONDENSATION;
D O I：
10.1021/ol501766m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel tandem oxidative conversion of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines to phenazines has been achieved under transition-metal-free, mild conditions using K2S2O8 or DDQ as the oxidizing agent. The transformation proceeds through oxidative removal of a benzylic methylene group by C-C and C-N bond cleavage followed by a new aryl C-N bond formation under radical conditions.
引用
收藏
页码：4392 / 4395
页数：4
相关论文
共 50 条
  • [41] Bifunctional Transition Metal-Based Molecular Catalysts for Asymmetric C-C and C-N Bond Formation
    Ikariya, Takao
    Gridnev, Ilya D.
    TOPICS IN CATALYSIS, 2010, 53 (13-14) : 894 - 901
  • [42] Synthesis of Indazoles and Azaindazoles by Intramolecular Aerobic Oxidative C-N Coupling under Transition-Metal-Free Conditions
    Hu, Jiantao
    Xu, Huacheng
    Nie, Pengju
    Xie, Xiaobo
    Nie, Zongxiu
    Rao, Yu
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (14) : 3932 - 3938
  • [43] Difunctionalization of the C-N Bond through tert-Butylnitrite-Initiated C-N Cleavage of 1,2,3,4-Tetrahydroisoquinolines and N,N'-Diarylimidazolidines under Transition-Metal-Free Conditions
    Sun, Zheng
    Ji, Honghe
    Shao, Yu
    He, Kaixuan
    Zhang, Yuxian
    Yuan, Yu
    Jia, Xiaodong
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (19): : 12292 - 12300
  • [44] Supported aqueous phase catalysts for the C-C and C-N bond formation
    dos Santos, S
    Quignard, F
    Sinou, D
    Choplin, A
    PREPARATION OF CATALYSTS VII, 1998, 118 : 91 - 97
  • [45] Ru/Ceria catalyzes the C-C/C-N bond formation reactions
    An, Jinghua
    Wang, Feng
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [46] A new photochemical approach to benzylic polyradicals through C-N bond cleavage of a pyridinyl radical
    Mori, H
    Kozaki, M
    Sato, K
    Takui, T
    Okada, K
    TETRAHEDRON LETTERS, 1998, 39 (35) : 6315 - 6316
  • [47] Influence of Biaryl Phosphine Structure on C-N and C-C Bond Formation
    Pratap, Ramendra
    Parrish, Damon
    Gunda, Padmaja
    Venkataraman, D.
    Lakshman, Mahesh K.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) : 12240 - 12249
  • [48] Templated C-C and C-N Bond Formation Facilitated by a Molybdenum(VI) Metal Center
    Zwettler, Niklas
    Dupe, Antoine
    Schachner, Joerg A.
    Belaj, Ferdinand
    Moesch-Zanetti, Nadia C.
    INORGANIC CHEMISTRY, 2015, 54 (24) : 11969 - 11976
  • [49] Heme-Enzymatic Biocatalysis for C-C or C-N Bond Formation
    Weng, He
    Huang, Meilan
    CHEMCATCHEM, 2024, 16 (21)
  • [50] Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization
    Kantak, Abhishek A.
    DeBoef, Brenton L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
12345