Synthesis and reactivity of new trifluoromethylated azacyanines starting from 3-(1-amino-2,2,2-trifluororoethylidene)pyrrolidin-2-ones

被引：0
|
作者：
Bouillon, JP
Janousek, Z
Viehe, HG
机构：
来源：
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1996年 / 133卷 / 05期
关键词：
enamine; pyrrolidin-2-one; 4-azacyanine; pyrimidine; pyrimidin-2-one; 1,2,4-triazepine;
D O I：
暂无
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The trifluoromethylated enamines 4 and 5 obtained from 3-trifluoroacetyl-pyrrolidinone 1 and ammonia or methylamine, are good precursors for the synthesis of new 4-azapentamethine cyanines 8-10. These 1,5-bis-electrophiles condense with ammonia or phenylhydrazine to give 5H-pyrrolo[2,3-d] pyrimidines 18, 19, pyrimidinone 20 and pyrrolo-[3,2-f]-1,2,4-triazepines 21, 22. The structure and configuration of all the heterocycles are confirmed by their NMR and UV/vis data and by comparison with analogous compounds.
引用
收藏
页码：501 / 508
页数：8
相关论文
共 50 条
  • [1] Synthesis of 3-substituted pyrrolidin-2-ones and 3-substituted piperidin-2-ones from esters
    Brunotte, Lara
    Beckmann, Lars
    Ljiljanic, Marko
    Opatz, Till
    ARKIVOC, 2024,
  • [2] Synthesis and spectral features of new 1-alkyl-5-(indol-2(3)-yl)pyrrolidin-2-ones
    Mysova, N. E.
    Kovrov, A. E.
    Sadovoy, A. V.
    Sviridova, L. A.
    Golubeva, G. A.
    Vorozhtsov, N. I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 48 (11) : 1634 - 1640
  • [3] Synthesis and spectral features of new 1-alkyl-5-(indol-2(3)-yl)pyrrolidin-2-ones
    N. E. Mysova
    A. E. Kovrov
    A. V. Sadovoy
    L. A. Sviridova
    G. A. Golubeva
    N. I. Vorozhtsov
    Chemistry of Heterocyclic Compounds, 2013, 48 : 1634 - 1640
  • [4] SYNTHESIS AND ANTIINFLAMMATORY ACTIVITIES OF 3-(3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENE)PYRROLIDIN-2-ONES
    IKUTA, H
    SHIROTA, H
    KOBAYASHI, S
    YAMAGISHI, Y
    YAMADA, K
    YAMATSU, I
    KATAYAMA, K
    JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) : 1995 - 1998
  • [5] Efficient synthesis of new 1-[alkyl(aryl)]-5-(3,3,3-trihalo-2-oxopropylidene) pyrrolidin-2-ones
    Flores, Alex F. C.
    Flores, Darlene C.
    Oliveira, Graciela
    Pizzuti, Lucas
    da Silva, Rubia M. S.
    Martins, Marcos A. P.
    Bonacorso, Helio G.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2008, 19 (01) : 184 - 193
  • [6] STEREOCONTROLLED SYNTHESIS OF 3,5-DIALKYL-4-AMINO PYRROLIDIN-2-ONES FROM BETA-LACTAMS AS CHIRAL TEMPLATES
    PALOMO, C
    COSSIO, FP
    CUEVAS, C
    ODRIOZOLA, JM
    ONTORIA, JM
    TETRAHEDRON LETTERS, 1992, 33 (33) : 4827 - 4830
  • [7] REGIOSELECTIVE SYNTHESIS OF 1-ALKYL-5-(INDOL-3-YL- AND-2-YL)PYRROLIDIN-2-ONES FROM AVAILABLE REAGENTS
    Sadovoy, A. V.
    Kovrov, A. E.
    Golubeva, G. A.
    Sviridova, L. A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 46 (10) : 1215 - 1223
  • [8] UNCONVENTIONAL NUCLEOTIDE ANALOGS .9. N-SUBSTITUTED "3-(PYRIMIDIN-1-YL)PYRROLIDIN-2-ONES
    KOOMEN, GJ
    PANDIT, UK
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (18): : 1929 - 1933
  • [9] Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2-ones from available reagents
    A. V. Sadovoy
    A. E. Kovrov
    G. A. Golubeva
    L. A. Sviridova
    Chemistry of Heterocyclic Compounds, 2011, 46 : 1215 - 1223
  • [10] Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
    Rodriguez, Jose F.
    Zhang, Anji
    Arora, Ramon
    Lautens, Mark
    ORGANIC LETTERS, 2021, 23 (19) : 7540 - 7544
12345