Green metal-free synthesis of spiro-fused 3,4-pyrazolo[4,3:5,6]pyrido[2,3-d]pyrimidine derivatives via deamination cyclization reactions in aqueous medium

被引:8
|
作者
Dai, Lei [1 ]
Mao, Kaimin [1 ]
Pan, Zhengbing [1 ]
Rong, Liangce [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Pyrazolo[4 ' 3 ':5,6]pyrido[2,3-d] pyrimidine; Green synthesis; Deamination reaction; Aqueous medium; Spiro compound; ONE-POT SYNTHESIS; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; CATALYST; SPIROOXINDOLE; INHIBITORS; HETEROCYCLES; DISCOVERY; ACID; NANOPARTICLES;
D O I
10.1007/s11164-018-3642-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A green metal-free synthesis of spiro-fused 3,4-pyrazolo[4,3:5,6]pyrido[2,3-d]pyrimidine derivatives via deamination cyclization reactions of isatins, substituted 1H-pyrazol-5-amine, and 6-aminopyrimidine-2,4(1H,3H)-dione or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione in aqueous medium is reported. This is an efficient route for synthesis of the target products by deamination cyclization reaction. The other advantages of this process are high yield, easy separation, wide substrate range, and environmental friendliness.
引用
收藏
页码:769 / 788
页数:20
相关论文
共 50 条
  • [1] Green metal-free synthesis of spiro-fused 3,4′-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine derivatives via deamination cyclization reactions in aqueous medium
    Lei Dai
    Kaimin Mao
    Zhengbing Pan
    Liangce Rong
    Research on Chemical Intermediates, 2019, 45 : 769 - 788
  • [2] Synthesis of novel spiro-fused pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines
    Fazlelahi, Hadi Z.
    Moghadam, Peyman N.
    Baradarani, Mehdi M.
    Joule, John A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (10) : 3673 - 3684
  • [3] REACTIONS OF BENZOYLISOTHIOCYANATE WITH ACETOACETANILIDE - SYNTHESIS OF PYRAZOLE, PYRIDINE, PYRIMIDINE, PYRAZOLO[3,4-D]-PYRIMIDINE, PYRAZOLO[4,3-D]PYRIMIDINE AND PYRIDO[4,3-D]OXAZINE DERIVATIVES
    MOHAREB, RM
    AZIZ, SI
    ABDELSAYED, NI
    ELABLACK, FZ
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1993, 58 (04) : 947 - 953
  • [4] Synthesis of pyrazolo[3',4':5,6]pyrido[2,3-d]pyrimidines
    Ahluwalia, VK
    Dahiya, A
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (11): : 1208 - 1210
  • [5] An Efficient Four-component Synthesis of Spiro[indoline-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine]triones
    Ghahremanzadeh, Ramin
    Moghaddam, Mojtaba Mirhosseini
    Bazgir, Ayoob
    Akhondi, Mohammad Mehdi
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (02) : 321 - 326
  • [6] Synthesis of pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidine derivatives for antiviral evaluation
    Shamroukh, Ahmed H.
    Zaki, Magdi E. A.
    Morsy, Eman M. H.
    Abdel-Motti, Faiza M.
    Abdel-Megeid, Farouk M. E.
    ARCHIV DER PHARMAZIE, 2007, 340 (05) : 236 - 243
  • [7] Synthesis and pharmacological evaluation of pyrazolo[3,4-b]pyridine and pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidines
    Jachak, M. N.
    Avhale, Appasaheb
    DRUGS OF THE FUTURE, 2007, 32 : 38 - 38
  • [8] A simple synthesis of furo[3′,4′:5,6]pyrido[2,3-d]pyrimidine derivatives through multicomponent reactions in water
    Tu, Shu-Jiang
    Zhang, Yan
    Jiang, Hong
    Jiang, Bo
    Zhang, Jun-Yong
    Jia, Run-Hong
    Shi, Feng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (09) : 1522 - 1528
  • [9] A Novel Method for the Synthesis of Spiro[indoline-Pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine]triones by Alum as a Reusable Catalyst
    Shirvan, Sadif A.
    Ghahremanzadeh, Ramin
    Moghaddam, Mojtaba Mirhosseini
    Bazgir, Ayoob
    Zarnani, Amir Hassan
    Akhondi, Mohammad Mehdi
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) : 951 - 954
  • [10] One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives
    Bazgir, Ayoob
    Khanaposhtani, Maryam Mohammadi
    Soorki, Ali Abolhasani
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (21) : 5800 - 5803