Simple and green synthesis of 3-acyl-pyrazolo[1,5-a]pyridines: [3+2] through cycloaddition of N-aminopyridines on enaminones

被引：0
|
作者：
Redon, Sebastien [1 ]
Vanelle, Patrice [1 ]
机构：
[1] Aix Marseille Univ, Inst Chim Radicalaire ICR, Fac Pharm, CNRS UMR 7273,Equipe Pharmaco Chim Radicalaire LPC, 27 Bd Jean Moulin, Marseille, France
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2024年 / 61卷 / 07期
关键词：
DERIVATIVES; ANTAGONISTS; INHIBITORS; DISCOVERY; DESIGN; POTENT; SAR;
D O I：
10.1002/jhet.4851
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practicable method is described for the synthesis of 3-acyl-pyrazolo[1,5-a]pyridines from N-aminopyridines and easily available enaminones via a [3+2] cycloaddition. The reactions proceed well with a broad scope, without using additive (base or oxidant).
引用
收藏
页码：1200 / 1205
页数：6
相关论文
共 50 条
  • [41] A new synthetic route to fluorinated pyrazolo[3,4-b]pyridines and their use in the preparation of novel pyrido[2′,3′:3,4]pyrazolo[1,5-a] pyrimidines
    Reddy, ACS
    Narsaiah, B
    Venkataratnam, RV
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1997, 86 (02) : 127 - 130
  • [42] T3P-Mediated N-N Cyclization for the Synthesis of 1,2,4-Triazolo[1,5-a]pyridines
    Ayothiraman, Rajaram
    Bandaru, Durgarao
    Paranthaman, Ranjitha
    Fenster, Michael
    Eastgate, Martin D.
    Vaidyanathan, Rajappa
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (11) : 2510 - 2515
  • [43] A facile method for the synthesis of novel fluorinated pyrido [2′,3′:3,4] pyrazolo [1,5-a] pyrimidines
    Krishnaiah, A
    Narsaiah, B
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (02) : 183 - 187
  • [44] Synthesis of 3-and 2,3-substituted pyrazolo[1,5-a][1,10]phenanthrolines
    Viktoriya А. Sannikova
    Igor R. Filippov
    Oleg Yu. Karmatskikh
    Mikhail А. Panfilov
    Rodion V. Andreev
    Aleksey Yu. Vorob’ev
    [J]. Chemistry of Heterocyclic Compounds, 2020, 56 : 1042 - 1047
  • [45] Synthesis of 3-and 2,3-substituted pyrazolo[1,5-a][1,10]phenanthrolines
    Sannikova, Viktoriya A.
    Filippov, Igor R.
    Karmatskikh, Oleg Yu.
    Panfilov, Mikhail A.
    Andreev, Rodion V.
    Vorob'ev, Aleksey Yu.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 1042 - 1047
  • [46] Synthesis of 3-substituted imidazo[1,5-a]pyridines having 1-(N-picolinamidin-2-yl) group
    Fulwa, Vijendra Kumar
    Manivannan, Vadivelu
    [J]. TETRAHEDRON, 2012, 68 (21) : 3927 - 3931
  • [47] Chemistry of 2-arylhydrazonopropanals:: Novel synthesis of 1,6-dihydropyridazines and 5-heteroaryl substituted pyrazolo[1,5-a]pyrimidines and pyrazolo [3,4-b]pyridines
    Abdel-Khalik, MM
    Agamy, SM
    Elnagdi, MH
    [J]. SYNTHESIS-STUTTGART, 2001, (12): : 1861 - 1865
  • [48] Simple access toward 3-halo- and 3-nitro-pyrazolo [1,5-a]pyrimidines through a one-pot sequence
    Castillo, Juan-Carlos
    Rosero, Hernan-Alejandro
    Portilla, Jaime
    [J]. RSC ADVANCES, 2017, 7 (45): : 28483 - 28488
  • [49] Divergent Assembly of Functionalized Pyrazolo[1,5-a]pyridine Derivatives via [3+2] Cyclization of N-Aminopyridinium Salts with Various Unsaturated Hydrocarbons
    Liu, Xiang
    Ma, Shaohong
    Yan, Shi
    Shi, Xiaotian
    Li, Shuting
    Ma, Yanlong
    Cao, Hua
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2024,
  • [50] Copper-catalyzed [3+2] cycloaddition reactions: synthesis of substituted pyrazolo[1,5-c] quinazolines with N-iminoquinazolinium ylides and olefins as starting materials
    Feng, Haiyan
    Wang, Tao
    Chen, Songtao
    Huang, Yangfei
    Yu, Weijie
    Huang, Yuanyuan
    Xiong, Fei
    [J]. RSC ADVANCES, 2016, 6 (98): : 95774 - 95779
12345