Synthesis of purine and 2-aminopurine conjugates bearing the fragments of heterocyclic amines at position 6

被引:7
作者
Gruzdev, Dmitry A. [1 ]
Musiyak, Vera V. [1 ]
Chulakov, Evgeny N. [1 ]
Levit, Galina L. [1 ]
Krasnov, Victor P. [1 ]
机构
[1] Russian Acad Sci, Ural Branch, IYa Postovsky Inst Organ Synth, Ekaterinburg 620990, Russia
基金
俄罗斯科学基金会;
关键词
2-amino-6-chloropurine; 6-chloropurine; aromatic nucleophilic substitution; catalysis; heterocyclic amines; SOLVOLYTIC DECOMPOSITIONS; TRIFLUOROACETIC-ACID; NUCLEOSIDE ANALOGS; KINETIC RESOLUTION; KINASE INHIBITORS; HYDROLYSIS; MECHANISMS; LIBRARIES;
D O I
10.1007/s10593-015-1767-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel N-(purin-6-yl)- and N-(2-aminopurin-6-yl) derivatives of heterocyclic amines was synthesized. It was found that preferred preparative method for N-(purin-6-yl) derivatives of heterocyclic amines is interaction of 6-chloropurine with heterocyclic amines without any catalyst; whereas N-(2-aminopurin-6-yl) derivatives were obtained in the moderate-to-high yields while heating 2-amino-6-chloropurine and heterocyclic amines in water in the presence of sulfuric acid.
引用
收藏
页码:738 / 744
页数:7
相关论文
共 38 条
  • [1] DELOCALIZATION, CONFORMATION AND BASICITY OF ANILINES
    AHLBRECHT, H
    DUBER, EO
    EPSZTAJN, J
    MARCINKOWSKI, RMK
    [J]. TETRAHEDRON, 1984, 40 (07) : 1157 - 1165
  • [2] Banks K., 1944, J AM CHEM SOC, V66, P1127
  • [3] Banks K., 1944, J AM CHEM SOC, V66, P1131
  • [4] Berger J., US Patent, Patent No. 5958934
  • [5] Synthesis and antiproliferative activity of 6-phenylaminopurines
    Canela, Maria-Dolores
    Liekens, Sandra
    Camarasa, Maria-Jose
    Maria Priego, Eva
    Perez-Perez, Maria-Jesus
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 87 : 421 - 428
  • [6] Trifluoroacetic Acid in 2,2,2-Trifluoroethanol Facilitates SNAr Reactions of Heterocycles with Arylamines
    Carbain, Benoit
    Coxon, Christopher R.
    Lebraud, Honorine
    Elliott, Kristopher J.
    Matheson, Christopher J.
    Meschini, Elisa
    Roberts, Amy R.
    Turner, David M.
    Wong, Christopher
    Cano, Celine
    Griffin, Roger J.
    Hardcastle, Ian R.
    Golding, Bernard T.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (08) : 2311 - 2317
  • [7] CARTER CE, 1956, J BIOL CHEM, V223, P139
  • [8] Synthesis and application of functionally diverse 2,6,9-trisubstituted purine libraries as CDK inhibitors
    Chang, YT
    Gray, NS
    Rosania, GR
    Sutherlin, DP
    Kwon, S
    Norman, TC
    Sarohia, R
    Leost, M
    Meijer, L
    Schultz, PG
    [J]. CHEMISTRY & BIOLOGY, 1999, 6 (06): : 361 - 375
  • [9] NUCLEOPHILIC DISPLACEMENT REACTIONS IN AROMATIC SYSTEMS .3. KINETICS OF THE REACTIONS OF CHLORONITROPYRIDINES AND CHLOROPYRIMIDINES WITH PIPERIDINE, MORPHOLINE, PYRIDINE, AND ANILINE
    CHAPMAN, NB
    REES, CW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1954, (APR): : 1190 - 1196
  • [10] Charushin V. N., RU Patent, Patent No. 2434005