A Convenient Synthesis of 1-Aryl- and 2-Aryl-Substituted Indazolones via Intramolecular C-N Coupling Promoted by KOt-Bu

被引：12
|
作者：
Wang, Wei-juan [1 ]
Chen, Jia-hua [1 ]
Chen, Zi-cong [1 ]
Zeng, Yu-feng [1 ]
Zhang, Xue-jing [1 ]
Yan, Ming [1 ]
Chan, Albert S. C. [1 ]
机构：
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Inst Drug Synth & Pharmaceut Proc, Guangzhou 510006, Guangdong, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 20期
基金：
中国国家自然科学基金;
关键词：
indazolone; C-N coupling; potassium tert-butoxide; radical reaction; 2-halobenzohydrazide; KETOHEXOKINASE INHIBITORS; BIOLOGICAL EVALUATION; 1-ARYL-1H-INDAZOLES; SELECTIVITY; AMINATION; CATALYST; RECEPTOR; MURINE; SERIES;
D O I：
10.1055/s-0035-1562430
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method for the synthesis of 1-arylindazolones and 2-arylindazolones from N'-aryl-2-halobenzohydrazides promoted by KOt-Bu was developed. The difference of 2-halogen substituent exerted a significant effect on the distribution of the products. Two distinct reaction pathways are proposed for the generation of 1-arylindazolones and 2-arylindazolones, respectively.
引用
收藏
页码：3551 / 3558
页数：8
相关论文
共 50 条
  • [1] KOt-Bu promoted homocoupling and decomposition of N′-aryl acylhydrazines: synthesis of unsymmetric N′,N′-diaryl acylhydrazines
    Wang, Wei-juan
    Zhang, Ting
    Duan, Li-jun
    Zhang, Xue-jing
    Yan, Ming
    TETRAHEDRON, 2015, 71 (48) : 9073 - 9080
  • [2] Synthesis of 2-Aryl-Substituted Chromans by Intramolecular C-O Bond Formation
    Wang, Yu
    Franzen, Robert
    SYNLETT, 2012, (06) : 925 - 929
  • [3] Facile and convenient synthesis of aryl hydrazines via copper-catalyzed C-N cross-coupling of aryl halides and hydrazine hydrate
    Kurandina, Dania V.
    Eliseenkov, Eugene V.
    Ilyin, Petr V.
    Boyarskiy, Vadim P.
    TETRAHEDRON, 2014, 70 (26) : 4043 - 4048
  • [4] Chiral Arylated Amines via C-N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
    Song, Geyang
    Yang, Liu
    Li, Jing-Sheng
    Tang, Wei-Jun
    Zhang, Wei
    Cao, Rui
    Wang, Chao
    Xiao, Jianliang
    Xue, Dong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (39) : 21536 - 21542
  • [5] Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C-N coupling reaction of aryl halides and α-aminoamides
    Min, Xiangting
    Li, Xiaoyu
    Wang, Yu
    Dong, Yawen
    Tang, Jingjing
    Wang, Jing
    Liu, Jianhui
    TETRAHEDRON, 2018, 74 (21) : 2561 - 2566
  • [6] Exploiting palladium-catalyzed cross-coupling for the synthesis of 2-aryl-substituted 1-aminocyclopropylphosphonates
    Makukhin, Nikolay N.
    Goulioukina, Nataliya S.
    Bessmertnykh-Lemeune, Alla G.
    Brandès, Stéphane
    Guilard, Roger
    Beletskaya, Irina P.
    Synthesis (Germany), 2014, 46 (21)
  • [7] Electrocatalytic Synthesis of Substituted Pyrazoles via Hypervalent Iodine Mediated Intramolecular C-N Coupling
    Paveliev, Stanislav A.
    Segida, Oleg O.
    Bityukov, Oleg, V
    Tang, Hai-Tao
    Pan, Ying-Ming
    Nikishin, Gennady, I
    Terent'ev, Alexander O.
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (22) : 3910 - 3916
  • [8] Exploiting Palladium-Catalyzed Cross-Coupling for the Synthesis of 2-Aryl-Substituted 1-Aminocyclopropylphosphonates
    Makukhin, Nikolay N.
    Goulioukina, Nataliya S.
    Bessmertnykh-Lemeune, Alla G.
    Brandes, Stephane
    Guilard, Roger
    Beletskaya, Irina P.
    SYNTHESIS-STUTTGART, 2015, 47 (02): : 279 - 288
  • [9] Synthesis of -Hydroxycarboxylic Acid Anilides via Copper-Catalyzed C-N Coupling of -Hydroxyamides with Aryl Halides
    Li, Zhijie
    Wen, Quan
    Zhou, Lihong
    Deng, Xingmei
    Zeng, Qingle
    SYNTHESIS-STUTTGART, 2015, 47 (23): : 3751 - 3757
  • [10] Direct synthesis of primary arylamines via C-N cross-coupling of aryl bromides and triflates with amides
    Romero, M.
    Harrak, Y.
    Basset, J.
    Orue, J. A.
    Pujol, M. D.
    TETRAHEDRON, 2009, 65 (10) : 1951 - 1956
12345