Microwave-assisted synthesis of substituted pyrazoles and pyrazolo [3,4-d]thiopyrimidines

被引:14
|
作者
Heravi, MM [1 ]
Nami, N [1 ]
Seifi, N [1 ]
Oskooie, HA [1 ]
Hekmatshoar, R [1 ]
机构
[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran, Iran
关键词
ethylcyanoacetate; malononitrile; pyrazolo[3,4-d]thiopyrimidine; triethyl orthoacetate; triethyl orthoformate;
D O I
10.1080/10426500500269646
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ethyl(ethoxymethylene)cyanoacetate and ethoxymethylene malononitrile were synthesized from the reaction of malononitrile or ethylcyanoacetate with triethyl ortho-formate or orthoacetate in N, N-dimethylacetamide under microwave irradiation. In a similar manner, substituted pyrazoles were synthesized from the reaction of ethyl (ethoxymethylene)cyanoacetate and ethoxymethylene malononitrile with phenylhydrazine. These pyrazoles were converted to pyrazolo[3,4-d]thiopyrimidines upon treatment with arylisothiocyanate and thiourea under microwave irradiation.
引用
收藏
页码:591 / 599
页数:9
相关论文
共 50 条
  • [1] Synthesis of pyrrolino[3,4-d]pyrazoles, pyrazoles, pyrazolo[5,4-d]pyrimidines and pyrazolo[3,4-d]pyrimidines
    Riheem, Nadia A. Abdel
    Rateb, Nora M.
    Eldin, Sanaa M.
    [J]. DRUGS OF THE FUTURE, 2007, 32 : 40 - 41
  • [2] Substituted pyrazolo[3,4-d]pyrimidines:: Microwave-assisted, solvent-free synthesis and biological evaluation
    Oliveira-Campos, Ana M. F.
    Sivasubramanian, Aravind
    Rodrigues, Ligia M.
    Seijas, Julio A.
    Pilar Vazquez-Tato, M.
    Peixoto, Francisco
    Abreu, Carlos G.
    Cidade, Honorina
    Oliveira, Ana Elizabete
    Pinto, Madalena
    [J]. HELVETICA CHIMICA ACTA, 2008, 91 (07) : 1336 - 1345
  • [3] Microwave-assisted synthesis of N1-and C3-substituted pyrazolo[3,4-d]pyrimidine libraries
    Todorovic, Nick
    Awuah, Emelia
    Shakya, Tushar
    Wright, Gerard D.
    Capretta, Alfredo
    [J]. TETRAHEDRON LETTERS, 2011, 52 (44) : 5761 - 5763
  • [4] Microwave-assisted protocols for the expedited synthesis of pyrazolo[1,5-a] and [3,4-d]pyrimidines
    Daniels, R. Nathan
    Kim, Kwangho
    Lebois, Evan P.
    Muchalski, Hubert
    Hughes, Mary
    Lindsley, Craig W.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (02) : 305 - 310
  • [5] Synthesis of some new pyrazolo[3,4-d]pyrimidines and pyrazolo[3,4-c]pyrazoles
    Ahluwalia, VK
    Dahiya, A
    Bala, M
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (08): : 848 - 851
  • [6] Synthesis of new aryl and heteroaromatic substituted pyridines, pyrazoles, pyrimidines and pyrazolo[3,4-d]pyridazines
    AlOmran, F
    AlAwadi, N
    AbouElKhair, A
    Elnagdi, MH
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1997, 29 (03) : 285 - 292
  • [7] SYNTHESIS AND REACTIONS OF SUBSTITUTED PYRAZOLO[3,4-D]PYRIMIDINES
    OERTEL, F
    VOGEL, D
    RICHTER, PH
    [J]. PHARMAZIE, 1992, 47 (04): : 251 - 254
  • [8] SYNTHESIS OF FUNCTIONALIZED PYRAZOLES AND PYRAZOLO[3,4-D]PYRIMIDINES AS POTENTIAL LEISHMANICIDES
    RAM, VJ
    HAQUE, N
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (06): : 521 - 524
  • [9] Microwave-assisted synthesis and structure-activity relationships of neuroactive pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives
    Nascimento-Junior, Nailton M.
    Mendes, Thaiana C. F.
    Leal, Daniella M.
    Correa, Claudia Maria N.
    Sudo, Roberto T.
    Zapata-Sudo, Gisele
    Barreiro, Eliezer J.
    Fraga, Carlos A. M.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) : 74 - 77
  • [10] Microwave-Assisted, Divergent Solution-Phase Synthesis of 1,3,6-Trisubstituted Pyrazolo[3,4-d]pyrimidines
    Liu, Jing
    Wang, Xiaodong
    [J]. ACS COMBINATORIAL SCIENCE, 2011, 13 (04) : 414 - 420