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 74 条
  • [11] Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition
    Cardillo, G
    Fabbroni, S
    Gentilucci, L
    Perciaccante, R
    Piccinelli, F
    Tolomelli, A
    [J]. TETRAHEDRON, 2004, 60 (23) : 5031 - 5040
  • [12] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver
    Casiraghi, G
    Zanardi, F
    Appendino, G
    Rassu, G
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 1929 - 1972
  • [13] Ciganek E., 1997, ORGANIC REACTIONS, V51, Ch, P201, DOI DOI 10.1002/0471264180.OR051.02
  • [14] Employing a robustness screen: rapid assessment of rhodium(III)-catalysed C-H activation reactions
    Collins, Karl D.
    Glorius, Frank
    [J]. TETRAHEDRON, 2013, 69 (36) : 7817 - 7825
  • [15] The intramolecular Morita-Baylis-Hillman-type alkylation reaction
    Cran, John W.
    Krafft, Marie E.
    Seibert, Kimberly A.
    Haxell, Thomas F. N.
    Wright, James A.
    Hirosawa, Chitaru
    Abboud, Khalil A.
    [J]. TETRAHEDRON, 2011, 67 (51) : 9922 - 9943
  • [16] A stereodivergent synthesis of β-hydroxy-α-methylene lactones via vinyl epoxides
    Davoust, Marion
    Cantagrel, Frederic
    Metzner, Patrick
    Briere, Jean-Francois
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (11) : 1981 - 1993
  • [17] Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338
  • [18] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES
    DREWES, SE
    ROOS, GHP
    [J]. TETRAHEDRON, 1988, 44 (15) : 4653 - 4670
  • [19] Acrylamide in the Baylis-Hillman reaction: Expanded reaction scope and the unexpected superiority of DABCO over more basic tertiary amine catalysts
    Faltin, C
    Fleming, EM
    Connon, SJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) : 6496 - 6499
  • [20] Enantioselective Gold(I)-Catalyzed Hydrative Cyclizations of N-Propargyl-ynamides into 3,6-Dihydropyridinones
    Febvay, Julie
    Sanogo, Youssouf
    Retailleau, Pascal
    Gogoi, Manash Protim
    Sahoo, Akhila K.
    Marinetti, Angela
    Voituriez, Arnaud
    [J]. ORGANIC LETTERS, 2019, 21 (23) : 9281 - 9285