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
  • [31] Catalytic Hydrogenation of 3-Amino-6-(trifluoromethyl)-5,6-dihydropyridin-2(1H)-ones and Its Use in the Synthesis of Trifluoromethyl-Containing Mimetics of Ornithine and Thalidomide
    Tolmachova, Nataliya A.
    Dolovanyuk, Violetta G.
    Gerus, Igor I.
    Kondratov, Ivan S.
    Polovinko, Vitaliy V.
    Bergander, Klaus
    Haufe, Guenter
    [J]. SYNTHESIS-STUTTGART, 2011, (07): : 1149 - 1156
  • [32] Synthesis of 5-and 7-fluoroquinazolin-4(1H)-ones
    Layeva, A. A.
    Nosova, E. V.
    Lipunova, G. N.
    Trashakhova, T. V.
    Charushin, V. N.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2007, 56 (09) : 1821 - 1827
  • [33] Synthesis of 5-and 7-fluoroquinazolin-4(1H)-ones
    A. A. Layeva
    E. V. Nosova
    G. N. Lipunova
    T. V. Trashakhova
    V. N. Charushin
    [J]. Russian Chemical Bulletin, 2007, 56 : 1821 - 1827
  • [34] A One-Pot Biginelli Synthesis of 6-Unsubstituted 5-Aroylpyrimidin-2(1H)-ones and 6-Acetyl-1,2,4-triazin-3(2H)-ones
    Darwish, Elham Sayed
    Abdelhamid, Ismail Abdelshafy
    Nasra, Miead Adel
    Abdel-Gallil, Fathy Mohamed
    Fleita, Daisy Hanna
    [J]. HELVETICA CHIMICA ACTA, 2010, 93 (06) : 1204 - 1208
  • [35] THE SYNTHESIS OF NITROGEN-HETEROCYCLES VIA THE INTRAMOLECULAR KHAND REACTION - FORMATION OF TETRA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXAHYDRO-6H-2-PYRINDIN-6-ONES
    BROWN, SW
    PAUSON, PL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04): : 1205 - 1209
  • [36] Cyclizations of monocyclic 5-nitropyridin-2(1H)-ones
    N. N. Smolyar
    Yu. M. Yutilov
    [J]. Russian Journal of Organic Chemistry, 2008, 44 : 1205 - 1210
  • [37] Unexpected Synthesis of 5,6-Dihydropyridin-2(1H)-ones by a Domino Ugi/Aldol/Hydrolysis Reaction Starting from Baylis-Hillman Phosphonium Saks
    Zeng, Xiao-Hua
    Wang, Hong-Mei
    Ding, Ming-Wu
    [J]. ORGANIC LETTERS, 2015, 17 (09) : 2234 - 2237
  • [38] Cyclizations of monocyclic 5-nitropyridin-2(1H)-ones
    Smolyar, N. N.
    Yutilov, Yu. M.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (08) : 1205 - 1210
  • [39] 3-(α-Chlorobenzyl)quinoxalin-2(1H)-ones as Versatile Reagents for the Synthesis of 3-Benzylquinoxalin-2(1H)-ones and Thiazolo[3,4-a]quinoxalin-4(5H)-ones
    Mamedov, Vakhid A.
    Zhukova, Nataliya A.
    Syakaev, Victor V.
    Beschastnova, Tat'yana N.
    Kadyrova, Milyausha S.
    Isaeva, Anastasiya O.
    Mamedova, Sevil, V
    Gavrilova, Elena L.
    Latypov, Shamil K.
    Sinyashin, Oleg G.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (08) : 2221 - 2234
  • [40] DIVERGENT SYNTHESIS OF 5,6-AND 3,6-DIHYDROPYRIDIN-2(1H)-ONE VIA INTRAMOLECULAR KNOEVENAGEL CONDENSATION
    Bocardo-Bautista, Arturo
    Orea, Maria L.
    Juarez, Jorge R.
    Gnecco, Dino
    Aparicio, David M.
    Teran, Joel L.
    [J]. HETEROCYCLES, 2019, 98 (01) : 96 - 104