Alkoxy-5-nitrosopyrimidines: Useful Building Block for the Generation of Biologically Active Compounds

被引：22
作者：
Marchal, Antonio [1 ]
Nogueras, Manuel [1 ]
Sanchez, Adolfo [1 ]
Low, John N. [2 ]
Naesens, Lieve [3 ]
De Clercq, Erik [3 ]
Melguizo, Manuel [1 ]
机构：
[1] Univ Jaen, Inorgan & Organ Chem Dept, Jaen 23071, Spain
[2] Univ Aberdeen, Dept Chem, Aberdeen AB24 3UE, Scotland
[3] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 20期
关键词：
Nitrogen heterocycles; Nitrosation; Amination; Nucleophilic substitution; Antiviral agents; SOLID-PHASE SYNTHESIS; CYCLIN-DEPENDENT KINASE-1; PART; REGIOSELECTIVE; 4-AMINO-DE-CHLORINATION; DERIVATIVES; PYRIMIDINES; 2,4,6-TRICHLOROPYRIMIDINE; INHIBITORS; INTERPLAY; NMR;
D O I：
10.1002/ejoc.201000195
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several alkoxy-5-nitrosopyrimidines were synthesised and high regioselective and sequential nucleophilic aromatic substitution of methoxy groups in 2-amino-4,6-dimethoxy-5-nitrosopyrimidine was observed. The approach was applied to the synthesis of valuable polyfunctionalised aminopyrimidines capable of mimicking fused heterobicyclic derivatives of biological interest. In addition, new compounds were evaluated as antivirals and their usefulness as synthetic intermediates was demonstrated.
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收藏
页码：3823 / 3830
页数：8
相关论文
共 70 条
  • [1] THE ORIGINS OF THE DICHOTOMY OF AMINE EFFECTS IN AROMATIC NUCLEOPHILIC-SUBSTITUTION REACTIONS
    AKPOJIVI, RE
    EMOKPAE, TA
    HIRST, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (03): : 443 - 449
  • [2] Identification of novel purine and pyrimidine cyclin-dependent kinase inhibitors with distinct molecular interactions and tumor cell growth inhibition profiles
    Arris, CE
    Boyle, FT
    Calvert, AH
    Curtin, NJ
    Endicott, JA
    Garman, EF
    Gibson, AE
    Golding, BT
    Grant, S
    Griffin, RJ
    Jewsbury, P
    Johnson, LN
    Lawrie, AM
    Newell, DR
    Noble, MEM
    Sausville, EA
    Schultz, R
    Yu, W
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (15) : 2797 - 2804
  • [3] Solid-phase synthesis of 2,4-diaminopyrimidines via lewis acid-mediated aromatic nucleophilic substitution
    Arvanitis, EA
    Chadha, N
    Pottorf, RS
    Player, MR
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (03): : 414 - 419
  • [4] Solution-phase synthesis of a library of 3,5,7-trisubstituted 3H-[1,2,3]triazolo[4,5-d]pyrimidines
    Baindur, N
    Chadha, N
    Player, MR
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (05): : 653 - 659
  • [5] Barillari C, 2001, EUR J ORG CHEM, V2001, P4737, DOI 10.1002/1099-0690(200112)2001:24<4737::AID-EJOC4737>3.0.CO
  • [6] 2-1
  • [7] A regioselective approach to trisubstituted 2 (or 6)-arylaminopyrimidine-5-carbaldehydes and their application in the synthesis of structurally and electronically unique G∧C base precursors
    Beingessner, Rachel L.
    Deng, Bo-Liang
    Fanwick, Phillip E.
    Fenniri, Hicham
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03) : 931 - 939
  • [8] EXPERIMENTAL AND THEORETICAL INVESTIGATION OF C-NITROSO ROTATION IN 2-NITROSOIMIDAZOLES
    BOLTON, JL
    PETERSON, MR
    MCCLELLAND, RA
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (12): : 3044 - 3049
  • [9] PTERIDINES .3. UNAMBIGUOUS SYNTHESES OF XANTHOPTERIN AND 2-AMINO-4-HYDROXY-6-METHYLPTERIDINE
    BOON, WR
    LEIGH, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1951, (JUN): : 1497 - 1501
  • [10] BOON WR, 1952, J CHEM SOC, P1532
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