Synthesis and structural insights of novel 2-diethylamino-6-methyl-4(3H)-pyrimidinones

被引:0
|
作者
Craciun, L [1 ]
Kovacs, D [1 ]
Craciun, R [1 ]
Mager, S [1 ]
机构
[1] Univ Babes Bolyai, Dept Organ Chem, R-3400 Cluj Napoca, Romania
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of three previously unknown 2-diethylamino-6-methyl-4(3H)-pyrimidinones via the condensation reaction of ethyl 2-alkylacetoacetates with N,N-diethylguanidine is described. The reported compounds, 5-ethyl- (1) under bar, 5-n-propyl-(2) under bar, and 5-n-butyl-2-diethylamino-6-methyl-4(3H)-pyrimidinone (3) under bar, were characterized by H-1 and C-13 NMR, IR, UV and mass spectrometry, and their tautomerism is discussed and compared with literature data for similar compounds. The results of NOE experiments suggest that in solution (1) under bar (2) under bar and (3) under bar, exist predominantly as the 4(3H)-lactam tautomers (N3).
引用
收藏
页码:157 / 162
页数:6
相关论文
共 50 条
  • [32] Molecular Structure of an Isocytosine Analog: Combined X-ray Structural and Computational Study of 2-Diethylamino-6-methyl-5-n-propyl-4(3H)-pyrimidinone
    Liliana Crăciun
    Radu Custelcean
    Sorin Mager
    Structural Chemistry, 1999, 10 : 303 - 310
  • [33] NOVEL RING EXPANSION REACTION OF 4-AMINOANTIPYRINES TO 5-AMINO-4(3H)-PYRIMIDINONES
    UEDA, T
    ODA, N
    ITO, I
    HETEROCYCLES, 1977, 8 : 263 - 268
  • [34] SYNTHESIS OF [3H]FALLYPRIDE USING [3H]METHYL NOSYLATE
    Hess, T.
    Meisterhans, C.
    Roesch, F.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2009, 52 : S353 - S353
  • [35] A SHORT SYNTHESIS OF 4-AZAINDOL-2(3H)-ONES AND 6-AZAINDOL-2(3H)-ONES
    DAISLEY, RW
    HANBALI, JR
    SYNTHETIC COMMUNICATIONS, 1981, 11 (09) : 743 - 749
  • [36] A Novel Method for the Synthesis of 4(3H)-Quinazolinones
    Jing, Xiao-Bi
    Li, Zhen
    Pan, Xin
    Shi, Yao-Cheng
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2008, 55 (05) : 1145 - 1149
  • [37] A novel method for the synthesis of 4(3H)-quinazolinones
    Abdel-Jalil, RJ
    Voelter, W
    Saeed, M
    TETRAHEDRON LETTERS, 2004, 45 (17) : 3475 - 3476
  • [38] 2-methoxy-3-methyl-6-[(triphenylphosphoranylidene)amino]pyrimidin-4(3H)-one and 3-methyl-2-methylthio-6-[(triphenylphosphoranylidene)amino]pyrimidin-4(3H)-one
    Low, JN
    Ferguson, G
    Cobo, J
    Nogueras, M
    Sanchez, A
    Marchal, A
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 : 1355 - 1357
  • [39] An unexpected and efficient direct nucleophilic C-4 hydroxy substitution on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain
    Botta, M
    Occhionero, F
    Saladino, R
    Crestini, C
    Nicoletti, R
    TETRAHEDRON LETTERS, 1997, 38 (47) : 8249 - 8252
  • [40] SYNTHESIS AND REACTIONS OF 3-AMINO-2-METHYL-4(3H)-QUINAZOLINONE DERIVATIVES
    YASSIN, FA
    EISSA, AMF
    WASFY, AAF
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1994, 33 (12): : 1193 - 1196