Halogenation of Pyrazolo[1,5-a]Pyrimidines with NXS

被引：3
作者：
Sang, Tian [1 ]
Li, Chuntian [1 ]
Jia, Fan [1 ]
He, Jing [1 ]
Liu, Yan [1 ]
Vaccaro, Luigi [2 ]
Liu, Jichang [1 ]
Liu, Ping [1 ]
机构：
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi, Peoples R China
[2] Univ Perugia, Dipartimento Chim Biol & Biotecnol, Lab Green SOC, Perugia, Italy
来源：
POLYCYCLIC AROMATIC COMPOUNDS | 2023年 / 43卷 / 09期
基金：
中国国家自然科学基金;
关键词：
Halogenation; pyrimidine; synthesis; RECEPTOR; POTENT;
D O I：
10.1080/10406638.2022.2144906
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of halogenated systems for pyrazolo[1,5-a]pyrimidines have been developed. Selective transformations of pyrazolo[1,5-a]pyrimidines by mono- and di-iodination were achieved by varying the ratio of pyrazolo[1,5-a]pyrimidines to NIS. In addition, the reaction of pyrazolo[1,5-a]pyrimidines with NBS or NCS uniquely gave dibrominated or dichlorinated products. The wide range of substrates, good functional group tolerance and gram-scale synthesis further demonstrate the application potential of this reaction. This work provides an efficient method for the construction of structurally diverse halogenated pyrazolo[1,5-a]pyrimidine derivatives.
引用
收藏
页码：8037 / 8047
页数：11
相关论文
共 50 条
  • [31] Recyclization of 1H-Pyrrole-2,3-diones into pyrazolo-[1,5-a]pyrimidines by the action of aminopyrazole
    E. S. Denislamova
    Z. G. Aliev
    A. N. Maslivets
    Russian Journal of Organic Chemistry, 2009, 45 : 1572 - 1573
  • [32] Aminoazoles in Heterocycles Synthesis: II. Trifluoromethyl-containing Diketones in the Synthesis of Pyrazolo[1,5-a]pyrimidines
    E. E. Emelina
    A. A. Petrov
    A. V. Firsov
    Russian Journal of Organic Chemistry, 2001, 37 : 852 - 858
  • [33] Synthesis and biological activity evaluation of novel 3,5,7-trisubstituted pyrazolo[1,5-a]pyrimidines
    Vlkova, Kristyna
    Padrtova, Ruzena
    Gucky, Tomas
    Perina, Miroslav
    Reznickova, Eva
    Krystof, Vladimir
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2023, 80
  • [34] Recent synthetic methodologies for pyrazolo[1,5-a]pyrimidine
    Salem, Mohamed A.
    Helal, Mohamed H.
    Gouda, Moustafa A.
    Abd EL-Gawad, Hala H.
    Shehab, Marwa A. M.
    El-Khalafawy, Abeer
    SYNTHETIC COMMUNICATIONS, 2019, 49 (14) : 1750 - 1776
  • [35] Synthesis of pyrazolo [1,5-a] pyrimidines by the reaction of β-dicarbonyl compounds with 3,5-diamino-4-nitropyrazole
    Makarov V.A.
    Tafeenko V.A.
    Granik V.G.
    Chemistry of Heterocyclic Compounds, 1998, 34 (12) : 1423 - 1427
  • [36] Design, synthesis and bioevaluation of 2,7-diaryl-pyrazolo[1,5-a]pyrimidines as tubulin polymerization inhibitors
    Liu, Runlai
    Zhang, Shuai
    Huang, Mingxin
    Guo, Zhenpeng
    Li, Long
    Li, Mi
    Wu, Lan
    Guan, Qi
    Zhang, Weige
    BIOORGANIC CHEMISTRY, 2021, 115
  • [37] Synthesis of Pyrazolo[1,5-a]pyridinyl, Pyrazolo[1,5-a]quinolinyl, and Pyrazolo[5,1-a]isoquinolinyl Sulfonyl Fluorides via a [3+2] Annulation
    Wu, Wen-Qian
    Qin, Hua-Li
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05) : 3266 - 3276
  • [38] An overview of the most used synthetic pathways of 1,2,4-triazolo[1,5-a] pyrimidines
    Zedan, Mohamed N.
    Shoman, Mai E.
    Abdel-Aziz, Mohamed
    Abdel-Rahman, Hamdy M.
    RESULTS IN CHEMISTRY, 2024, 12
  • [39] I2-Catalyzed Multicomponent Reactions for Accessing Densely Functionalized Pyrazolo[1,5-a]pyrimidines and Their Disulphenylated Derivatives
    Sun, Jun
    Qiu, Jiang-Kai
    Jiang, Bo
    Hao, Wen-Juan
    Guo, Cheng
    Tu, Shu-Jiang
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08) : 3321 - 3328
  • [40] Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo [1,5-a]pyrimidines as novel larotrectinib analogs
    Attia, Mohamed H.
    Elrazaz, Eman Z.
    El-Emam, Soad Z.
    Taher, Azza T.
    Abdel-Aziz, Hatem A.
    Abouzid, Khaled A. M.
    BIOORGANIC CHEMISTRY, 2020, 94
12345