An efficient regioselective copper catalyzed multi-component synthesis of 1,3-disubstituted pyrazoles

被引:18
|
作者
Raghunadh, Akula [1 ]
Meruva, Suresh Babu [1 ]
Mekala, Ramamohan [1 ]
Rao, K. Raghavendra [1 ]
Krishna, Thalishetti [1 ]
Chary, R. Gangadhara [1 ]
Rao, L. Vaikunta [2 ]
Kumar, U. K. Syam [3 ]
机构
[1] Dr Reddys Labs Ltd, Custom Pharmaceut Serv, Technol Dev Ctr, Hyderabad 500049, Andhra Pradesh, India
[2] Gitam Univ, GIS, Dept Chem, Visakhapatnam, Andhra Pradesh, India
[3] Dr Reddys Labs Ltd, Integrated Prod Dev, Hyderabad 500049, Andhra Pradesh, India
关键词
Pyrazoles; Multicomponent reaction; Michael addition; Cu catalyst and Ullmann cross-coupling reaction; 1,3-DIPOLAR CYCLOADDITIONS; SUBSTITUTED PYRAZOLES; ARYLATION; STRAIGHTFORWARD; CYCLIZATION; CELECOXIB; ULLMANN;
D O I
10.1016/j.tetlet.2014.03.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of unsymmetrically substituted 1,3-pyrazole derivatives has been developed via three-component coupling reaction involving 3-(dimethylamino)-1-phenylprop-2-en-1-one, hydrazine, and aryl halides in one pot process exhibiting high regioselectivity. The pyrazole synthesis proceeds via a sequential series of reactions such as Michael addition, heterocyclization, dehydration, and Ullmann cross-coupling. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2986 / 2990
页数:5
相关论文
共 50 条
  • [41] A palladium catalyzed asymmetric desymmetrization approach to enantioenriched 1,3-disubstituted isoindolines
    Dethe, Dattatraya H.
    Kumar, Vimlesh
    Shukla, Manmohan
    CHEMICAL SCIENCE, 2023, 14 (40) : 11267 - 11272
  • [42] Divergent synthesis of 1,3,5-tri and 1,3-disubstituted pyrazoles under transition metal-free conditions
    Ma, Liyao
    Ou, Pengcheng
    Huang, Xueliang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (33) : 6487 - 6491
  • [43] Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines
    Kim, Alexia N.
    Ngamnithiporn, Aurapat
    Welin, Eric R.
    Daiger, Martin T.
    Grunanger, Christian U.
    Bartberger, Michael D.
    Virgil, Scott C.
    Stoltz, Brian M.
    ACS CATALYSIS, 2020, 10 (05) : 3241 - 3248
  • [44] Copper-catalyzed tandem synthesis of [1,2,3]triazolo[5,1-a]isoquinolines and their transformation to 1,3-disubstituted isoquinolines
    Hu, Yuan-Yuan
    Hu, Jie
    Wang, Xiang-Chuan
    Guo, Li-Na
    Shu, Xing-Zhong
    Niu, Yan-Ning
    Liang, Yong-Min
    TETRAHEDRON, 2010, 66 (01) : 80 - 86
  • [46] THE H-1 AND C-13 NMR RULES FOR THE ASSIGNMENT OF 1,3-DISUBSTITUTED AND 1,5-DISUBSTITUTED PYRAZOLES - A REVISION
    BRUIX, M
    DEMENDOZA, J
    ELGUERO, J
    TETRAHEDRON, 1987, 43 (20) : 4663 - 4668
  • [47] Zinc acetate-mediated regioselective N-acylation of 1,3-disubstituted selenoureas
    Li, Xue
    Gan, Bin
    Peng, Zhixiang
    Mi, Zhisheng
    Xie, Yuanyuan
    JOURNAL OF CHEMICAL RESEARCH, 2018, (05) : 251 - 254
  • [48] Expeditious method for synthesis of symmetrical 1,3-disubstituted ureas and thioureas
    Perveen, S
    Hai, SMA
    Khan, RA
    Khan, KM
    Afza, N
    Sarfaraz, TB
    SYNTHETIC COMMUNICATIONS, 2005, 35 (12) : 1663 - 1674
  • [49] ORIGIN OF THE REGIOSELECTIVE LITHIATION OF 1,3-DISUBSTITUTED HETEROATOM AROMATICS - MNDO EVIDENCE FOR BIDENTATE COMPLEXATION
    SAA, JM
    DEYA, PM
    SUNER, GA
    FRONTERA, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) : 9093 - 9100
  • [50] A FACILE SYNTHESIS OF 1-MONOSUBSTITUTED AND UNSYMMETRICALLY 1,3-DISUBSTITUTED URACILS
    SINGH, H
    AGGARWAL, P
    KUMAR, S
    SYNTHESIS-STUTTGART, 1990, (06): : 520 - 522