Phosphine(III)-Triggered One-Pot Domino Sequences towards 5,6-Dihydropyridine-2-(1H)-One and Pyridine-2(1H)-One Scaffolds

被引:1
|
作者
Makra, Zsofia [1 ]
Madacsi, Ramona [1 ]
Martinek, Tamas A. [2 ]
Benyei, Attila [3 ]
Puskas, Laszlo G. [1 ]
Gyuris, Mario [1 ]
Kanizsai, Ivan [1 ]
机构
[1] AVIDIN Ltd, Also Kikoto Sor 11-D, H-6726 Szeged, Hungary
[2] Univ Szeged, Dept Med Chem, Dom Ter 8, H-6720 Szeged, Hungary
[3] Univ Debrecen, Dept Phys Chem, Lab Xray Diffract, Egyet Ter 1, H-4032 Debrecen, Hungary
关键词
Phosphine(III); One-pot domino synthesis; Mannich precursor; 5; 6-Dihydropyridine-2(1H)-one; Pyridine-2(1H)-one; BAYLIS-HILLMAN REACTION; VINYLOGOUS ALDOL REACTION; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; CATALYZED REACTION; ACRYLAMIDE; PHOSPHINE; DERIVATIVES; DIHYDROPYRIDINONE; ENHANCEMENT;
D O I
10.1002/adsc.202101370
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An elegant P(nBu)(3)-triggered synthetic approach has been developed towards multisubstituted 5,6-dihydropyridin-2(1H)-one and pyridin-2(1H)-one derivatives exploiting a domino process involving retro-Claisen/intra-MBH/Wittig/vinylogous aldol transformations as well as retro-Claisen/intra-MBH/ylide hydrolysis/oxidation sequences. This transformation demonstrates chemo- and regioselectivity as well as accessible high diversity enchancement in 17-90% isolated yield.
引用
收藏
页码:1134 / 1143
页数:10
相关论文
共 50 条
  • [11] Solvatochromic effect on photophysical properties of Quinoxalin-2(1H)-one and 3-Benzylquinoxalin-2(1H)-one
    R. Jdaa
    B. Benali
    A. El Assyry
    B. Lakhrissi
    Optical and Quantum Electronics, 2017, 49
  • [12] A new route to 5,6-dihydropyridine-2(1H)-thiones
    Fissyuk, AS
    Vorontsova, MA
    Temnikov, DV
    TETRAHEDRON LETTERS, 1996, 37 (29) : 5203 - 5206
  • [13] 6-Chloroquinolin-2(1H)-one
    Zhang, Chen-Guang
    Luo, Yang-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [14] 6-Nitroquinolin-2(1H)-one
    da Silva, LE
    Joussef, AC
    Foro, S
    Schmidt, B
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2992 - O2993
  • [15] 3-benzyl-5-bromopyrazin-2(1H)-one
    Alen, Jo
    Dobrzanska, Liliana
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O547 - U728
  • [16] Ultrasound-Promoted One-Pot, Four-Component Synthesis of Pyridin-2(1H)-One Derivatives
    Yang, Jinming
    Li, Qiang
    Zhang, Juanjuan
    Lin, Wei
    Wang, Juxian
    Wang, Yucheng
    Huang, Zhibin
    Shi, Daqing
    MOLECULES, 2013, 18 (12): : 14519 - 14528
  • [17] Synthesis and reactions of 4-trifluoromethyl-3-cyano pyridine-2(1H)-thione/one derivatives
    Rateb, Nora M.
    JOURNAL OF SULFUR CHEMISTRY, 2011, 32 (06) : 611 - 622
  • [18] (-)-1-Benzyl-4-[1(S)-phenylethylamino]-5,6-dihydropyridin-2(1H)-one
    Romero, N
    Terán, JL
    Gnecco, D
    Bernès, S
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2005, 61 : O2924 - O2926
  • [19] NEW SYNTHESIS OF SUBSTITUTED PYRIDINE-2(1H)-THIONES AND HETEROCYCLIC-COMPOUNDS STARTING FROM PYRIDINE-2(1H)-THIONES
    SHARANIN, YA
    PROMONENKOV, VK
    SHESTOPALOV, AM
    ZHURNAL ORGANICHESKOI KHIMII, 1982, 18 (09): : 2003 - 2005
  • [20] PHARMACOLOGICAL PROPERTIES OF 1-BENZYL-4-HYDROXYCYCLOHEPTIMIDAZOL-2(1H)-ONE A METABOLITE OF 1-BENZYLCYCLOHEPTIMIDAZOL-2(1H)-ONE (BENHEPAZONE)
    KOBAYASH.S
    TAKAGI, H
    ARZNEIMITTEL-FORSCHUNG, 1968, 18 (08): : 939 - &