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
  • [1] 6-trifluoromethanesulfonyloxy-4(3H)-pyrimidinones as versatile intermediates for the synthesis of 6-functionalized 4(3H)-pyrimidinones
    Taylor, EC
    Zhou, P
    Tice, CM
    TETRAHEDRON LETTERS, 1997, 38 (25) : 4343 - 4346
  • [2] SYNTHESIS AND BIOLOGICAL EVALUATION OF 6-SUBSTITUTED "3-ARYL-2-METHYL-4(3H)-PYRIMIDINONES
    GUPTA, KA
    SAXENA, AK
    JAIN, PC
    SRIMAL, RC
    KAR, K
    ANAND, N
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (04): : 384 - 387
  • [3] SYNTHESIS OF 5-AMINO-4(3H)-PYRIMIDINONES .2. SYNTHESIS OF 5-ACYL AND 5-ALKYLAMINO-3-PHENYL-6-METHYL-4(3H)-PYRIMIDINONES AND DETERMINATION OF THEIR ANALGESIC AND ANTIINFLAMMATORY ACTIVITIES
    UEDA, T
    SAKAKIBARA, J
    NAKAGAMI, J
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1983, 31 (12) : 4263 - 4269
  • [4] Synthesis of herbicidal 2-aryl-4-(3H)-pyrimidinones
    Tice, Colin M.
    Bryman, Lois M.
    Roemmele, Renee C.
    Taylor, Edward C.
    Zhou, Ping
    Jurczak, Janusz
    Jezewski, Artur
    ACS Symposium Series, 2002, 800 : 51 - 60
  • [5] SYNTHESIS OF 2-ALKOXY-6-ARYL-5-CYANO-4(3H)-PYRIMIDINONES
    PEREZ, MA
    SOTO, JL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (01) : 177 - 179
  • [6] SYNTHESIS AND REACTIONS OF 2,3-DIAMINO-4(3H)-PYRIMIDINONES AND 3-AMINO-2-HYDRAZINO-4(3H)-PYRIMIDINONES .1.
    HLAVKA, JJ
    BITHA, P
    LIN, Y
    STROHMEYER, T
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (05) : 1537 - 1541
  • [7] Regiocontrolled synthesis of 3-substituted-6-trifluoromethyl-4(3H)-pyrimidinones
    Tice, CM
    Bryman, LM
    TETRAHEDRON, 2001, 57 (14) : 2689 - 2700
  • [8] 2-Diethylamino-6-methylpyrimidin-4(3H)-one
    Wang, Mei-Yi
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2904 - U199
  • [9] Synthesis and tautomeric structure of 2-[N-aryl-2-oxo-2-arylethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinones
    Shawali, AS
    Farghaly, TA
    TETRAHEDRON, 2004, 60 (13) : 3051 - 3057
  • [10] Synthesis of herbicidal 2-aryl-4(3H)-pyrimidinones.
    Tice, CM
    Bryman, LM
    Roemmele, RC
    Taylor, EC
    Zhou, P
    Jurczak, J
    Jezewski, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U70 - U70