Decarboxylative Knoevenagel-Type Reactions on Tetronamides: Synthesis of 5-Ylidene-4-Amino-2(5H)-Furanones

被引：5
作者：
Ear, Alexandre [1 ,2 ]
Toum, Valerie [1 ,2 ]
Thorimbert, Serge [1 ,2 ]
Dechoux, Luc [1 ,2 ]
机构：
[1] Univ Paris 06, Sorbonne Univ, Inst Parisien Chim Mol, CNRS,UMR 8232, F-75005 Paris, France
[2] CNRS, Inst Parisien Chim Mol, UMR 8232, F-75005 Paris, France
来源：
SYNLETT | 2014年 / 25卷 / 12期
关键词：
Knoevenagel-Doebner reaction; -enaminoesters; tetronamides; 4-amino-2(5H)-furanones; basidalin; VINYLOGOUS URETHANE APPROACH; THERMAL REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; RING TRANSFORMATION; PRACTICAL SYNTHESIS; FACILE SYNTHESIS; DOEBNER REACTION; OKADAIC ACID; ESTERS; CONSTRUCTION;
D O I：
10.1055/s-0034-1378276
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A detailed account regarding the synthesis of 5-ylidene-2(5H)-furanones is given. The key step is a decarboxylative Knoevenagel-type reaction of tetronamides with various -functionalized aldehydes. The synthesis of protected basidalin is presented.
引用
收藏
页码：1713 / 1716
页数：4
相关论文
共 56 条
  • [1] Agami C, 2003, SYNTHESIS-STUTTGART, P859
  • [2] Agami C, 2002, SYNTHESIS-STUTTGART, P79
  • [3] Synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines
    Agami, C
    Dechoux, L
    Ménard, C
    Hebbe, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) : 7573 - 7576
  • [4] Agami C, 2001, SYNLETT, P1440
  • [5] Synthesis of enantiopure substituted aziridines by diastereoselective N-bromocyclization and nucleophile-mediated regioselective opening
    Agami, C
    Amiot, F
    Couty, F
    Dechoux, L
    [J]. TETRAHEDRON LETTERS, 1998, 39 (30) : 5373 - 5374
  • [6] Enantioselective synthesis of β-amino-diacids
    Alladoum, J
    Dechoux, L
    [J]. TETRAHEDRON LETTERS, 2005, 46 (47) : 8203 - 8205
  • [7] Aza-annulation of β-enaminolactones: application to the synthesis of enantiopure difunctionalized bicyclic lactams
    Alladourn, Jeanne
    Toum, Valerie
    Hebbe, Severine
    Kadouri-Puchot, Catherine
    Dechoux, Luc
    [J]. TETRAHEDRON LETTERS, 2009, 50 (06) : 617 - 619
  • [8] Stereoselective synthesis of functionalized butenolides by the photochemical rearrangement of [2,1]benzisoxazolequinone derivatives.
    Armesto, D
    RodriguezMorgade, S
    Ortiz, MJ
    Vazquez, P
    Torres, T
    [J]. TETRAHEDRON, 1997, 53 (09) : 3363 - 3368
  • [9] gem-dibromomethylarenes:: A convenient substitute for noncommercial aldehydes in the Knoevenagel-Doebner reaction for the synthesis of α,β-unsaturated carboxylic acids
    Augustine, John Kallikat
    Naik, Yanjerappa Arthoba
    Mandal, Ashis Baran
    Chowdappa, Nagaraja
    Praveen, Vinuthan B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) : 9854 - 9856
  • [10] gem-Dibromomethyl Aromatics: Efficient Aldehyde Equivalents in the Knoevenagel-Doebner Reaction
    Augustine, John Kallikat
    Naik, Yanjerappa Arthoba
    Poojari, Subba
    Chowdappa, Nagaraja
    Sherigara, Bailur Sheena
    Areppa, Kummara
    [J]. SYNTHESIS-STUTTGART, 2009, (14): : 2349 - 2356
123456