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
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 06期
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
  • [31] Pyridone Alkaloids from a Marine-Derived Fungus, Stagonosporopsis cucurbitacearum, and Their Activities against Azole-Resistant Candida albicans
    Haga, Asami
    Tamoto, Hiroki
    Ishino, Masahiro
    Kimura, Eriko
    Sugita, Takashi
    Kinoshita, Kaoru
    Takahashi, Kunio
    Shiro, Motoo
    Koyama, Kiyotaka
    [J]. JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04): : 750 - 754
  • [32] FUNCTIONALIZATION OF THE ALPHA-POSITION OF ACRYLATE SYSTEMS BY THE ADDITION OF CARBONYL-COMPOUNDS - HIGHLY PRESSURE-DEPENDENT REACTIONS
    HILL, JS
    ISAACS, NS
    [J]. TETRAHEDRON LETTERS, 1986, 27 (41) : 5007 - 5010
  • [33] Hillman A.B., 1972, German Patent, Patent No. 2155113
  • [34] Tandem Reaction of Allenoate Formation and Cyclization: Divergent Synthesis of Four- to Six-Membered Heterocycles
    Ji, Danqing
    Liu, Kai
    Sun, Jiangtao
    [J]. ORGANIC LETTERS, 2018, 20 (23) : 7708 - 7711
  • [35] Carbamoyl Pyridone HIV-1 Integrase Inhibitors 3. A Diastereomeric Approach to Chiral Nonracemic Tricyclic Ring Systems and the Discovery of Dolutegravir (S/GSK1349572) and (S/GSK1265744)
    Johns, Brian A.
    Kawasuji, Takashi
    Weatherhead, Jason G.
    Taishi, Teruhiko
    Temelkoff, David P.
    Yoshida, Hiroshi
    Akiyama, Toshiyuki
    Taoda, Yoshiyuki
    Murai, Hitoshi
    Kiyama, Ryuichi
    Fuji, Masahiro
    Tanimoto, Norihiko
    Jeffrey, Jerry
    Foster, Scott A.
    Yoshinaga, Tomokazu
    Seki, Takahiro
    Kobayashi, Masanori
    Sato, Akihiko
    Johnson, Matthew N.
    Garvey, Edward P.
    Fujiwara, Tamio
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (14) : 5901 - 5916
  • [36] A simple preparation of syn-NH-amide aldols and amide-Baylis-Hillman adducts via a Michael-aldol tandem process
    Kamimura, A
    Omata, Y
    Mitsudera, H
    Kakehi, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (24): : 4499 - 4504
  • [37] An efficient synthesis of Baylis-Hillman adducts of acrylamide: Pd-catalyzed hydration of Baylis-Hillman adducts of acrylonitrile
    Kim, Eun Sun
    Lee, Hyun Seung
    Kim, Jae Nyoung
    [J]. TETRAHEDRON LETTERS, 2009, 50 (46) : 6286 - 6289
  • [38] KUNDU MK, 1994, SYNLETT, P444
  • [39] Langer P, 2000, ANGEW CHEM INT EDIT, V39, P3049, DOI 10.1002/1521-3773(20000901)39:17<3049::AID-ANIE3049>3.0.CO
  • [40] 2-5
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