Silver-catalyzed decarboxylative cyclization for the synthesis of substituted pyrazoles from 1,2-diaza-1,3-dienes and α-keto acids

被引:17
作者
Katiyar, Sarita [1 ,2 ]
Kumar, Abhishek [1 ]
Sashidhara, Koneni, V [1 ,2 ,3 ]
机构
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Sect 10,Sitapur Rd, Lucknow 226031, Uttar Pradesh, India
[2] CSIR Human Resource Dev Ctr, Acad Sci & Innovat Res, CSIR HRDC Campus,Sect 19, Ghaziabad 201002, Uttar Pradesh, India
[3] CSIR Cent Drug Res Inst, Sophisticated Analyt Instrument Facil & Res, Sect 10,Sitapur Rd, Lucknow 226031, Uttar Pradesh, India
关键词
SITU GENERATED 1,2-DIAZA-1,3-DIENES; EFFICIENT; ACCESS; FUNCTIONALIZATION; CYCLOADDITION; SELECTIVITY; HYDRAZONES; ESTERS;
D O I
10.1039/d2cc01793h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A silver-catalyzed decarboxylative cyclization process has been developed for the synthesis of substituted pyrazoles from the readily available 1,2-diaza-1,3-dienes and alpha-keto acids. Under the optimized conditions, a series of multisubstituted pyrazoles were well prepared in moderate to good yields. In addition, the synthetic utility of this protocol has been demonstrated by synthesizing analogs of FDA approved drugs such as anti-inflammatory drug, lonazolac and antiobesity drug, rimonabant.
引用
收藏
页码:7297 / 7300
页数:4
相关论文
共 47 条
  • [21] Knorr L., 1883, CHEM BER-RECL, V16, P2597, DOI 10.1002/cber.188301602194
  • [22] Knorr L., 1888, BER, V21, P1205
  • [23] PIDA-mediated oxidative aromatic C-N bond cleavage: Efficient methodology for the synthesis of 1,2-diaza-1,3-dienes under ambient conditions
    Kumar, Abhishek
    Katiyar, Sarita
    Jaiswal, Arvind Kumar
    Kant, Ruchir
    V. Sashidhara, Koneni
    [J]. TETRAHEDRON LETTERS, 2021, 77
  • [24] Pyrazole containing natural products: Synthetic preview and biological significance
    Kumar, Vinod
    Kaur, Kamalneet
    Gupta, Girish Kumar
    Sharma, Anil Kumar
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 : 735 - 753
  • [25] Synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides
    Liu, Jie
    Fan, Chao
    Yin, Hongyu
    Qin, Chu
    Zhang, Guoting
    Zhang, Xu
    Yi, Hong
    Lei, Aiwen
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (17) : 2145 - 2147
  • [26] Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2
    Liu, Jie
    Liu, Qiang
    Yi, Hong
    Qin, Chu
    Bai, Ruopeng
    Qi, Xiaotian
    Lan, Yu
    Lei, Aiwen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) : 502 - 506
  • [27] Oxidation-Induced CH Functionalization: A Formal Way for CH Activation
    Liu, Yichang
    Yi, Hong
    Lei, Aiwen
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (08) : 692 - 697
  • [28] Oxidative Cross-Coupling Reactions between Two Nucleophiles†
    Lu, Lijun
    Li, Hao
    Lei, Aiwen
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (02) : 256 - 266
  • [29] Divergent Construction of Pyrazoles via Michael Addition of N-Arylhydrazones to 1,2-Diaza-1,3-dienes
    Mantenuto, Serena
    Mantellini, Fabio
    Favi, Gianfranco
    Attanasi, Orazio A.
    [J]. ORGANIC LETTERS, 2015, 17 (08) : 2014 - 2017
  • [30] Synthesis of Pyrazoles Utilizing the Ambiphilic Reactivity of Hydrazones
    Matsuzaki, Haruo
    Takeda, Norihiko
    Yasui, Motohiro
    Ito, Yuta
    Konishi, Keiji
    Ueda, Masafumi
    [J]. ORGANIC LETTERS, 2020, 22 (23) : 9249 - 9252