Synthesis of 5,6-dihydropyridin-2(1H)-ones,1,5,6,8,8a-hexahydroisoquinolin-3(2H)-ones and 4a,5,6,7,8,8a-hexahydroquinolin-2(1H)-ones by intramolecular Wittig reaction

被引:18
|
作者
Fisyuk, AS [1 ]
Poendaev, NV [1 ]
机构
[1] Omsk State Univ, Dept Organ Chem, Omsk 644077, Russia
关键词
5,6-dihydropyridin-2(1H)-one; Wittig reaction; intramolecular cyclization; N-(3-oxoalkyl)chloroacetamide;
D O I
10.3390/70200124
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
A new, universal and diastereospecific method has been developed for the synthesis of 5,6-dihydropyridin-2(1H)-ones, 1,5,6,8,8a-hexahydroisoquinolin-3(2H)-ones and 4a,5,6,7,8,8a-hexahydroquinolin-2(1H)-ones (4) based on the intramolecular Wittig cyclization of the triphenyphosphonium salts 2 derived from the N-(3-oxoalkyl)-chloroacetamides 1.
引用
收藏
页码:124 / 128
页数:5
相关论文
共 50 条
  • [1] 5,6-Dihydropyridin-2(1H)-ones and 5,6-dihydropyridine-2(1H)-thiones (review)
    Fisyuk A.S.
    Bundel' Yu.G.
    [J]. Chemistry of Heterocyclic Compounds, 1999, 35 (2) : 125 - 145
  • [2] SYNTHESIS OF 3-S-HETARYL-SUBSTITUTED PYRIDIN-2(1H)-ONES AND 5,6-DIHYDROPYRIDIN-2(1H)-ONES
    Fisyuk, A. S.
    Bogza, Y. P.
    Poendaev, N. V.
    Goncharov, D. S.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (07) : 844 - 849
  • [3] Synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones*
    A. S. Fisyuk
    Y. P. Bogza
    N. V. Poendaev
    D. S. Goncharov
    [J]. Chemistry of Heterocyclic Compounds, 2010, 46 : 844 - 849
  • [4] Preparation of 5,6-dihydropyridin-2(1H)-ones by intramolecular Wittig reaction on the basis of N-3-oxoalkylchloroacetamides
    Fisyuk, AS
    Poendaev, NV
    Bundel, YG
    [J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (02): : 281 - 282
  • [5] Synthesis of fluorinated 4-amino-5,6-dihydropyridin-2(1H)-ones
    Kosobokov, M. D.
    Struchkova, M. I.
    Dilman, A. D.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2014, 63 (02) : 549 - 551
  • [6] NEW SYNTHESIS OF 3-ARYL-5,6-DIHYDROPYRIDIN-2(1H)-ONES
    FISYUK, AS
    VORONTSOVA, MA
    IVANOV, SA
    [J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1994, (06): : 812 - 815
  • [7] A NEW SYNTHESIS OF 3-PHENYL-5,6-DIHYDROPYRIDIN-2(1H)-ONES
    FYSSIUK, AS
    VORONTSOVA, MA
    SAGITULLIN, RS
    [J]. MENDELEEV COMMUNICATIONS, 1993, (06) : 249 - 251
  • [8] Synthesis of fluorinated 4-amino-5,6-dihydropyridin-2(1H)-ones
    M. D. Kosobokov
    M. I. Struchkova
    A. D. Dilman
    [J]. Russian Chemical Bulletin, 2014, 63 : 549 - 551
  • [9] Synthesis of (S)-(+)-6-aryl-3-acetyl-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones
    N. M. Golovach
    V. A. Sukach
    M. V. Vovk
    [J]. Russian Journal of Organic Chemistry, 2010, 46 : 1070 - 1073
  • [10] Synthesis of (S)-(+)-6-aryl-3-acetyl-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones
    Golovach, N. M.
    Sukach, V. A.
    Vovk, M. V.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (07) : 1070 - 1073