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 50 条
  • [31] NEW, CONVENIENT SYNTHESIS OF 5,5-DIALKYL-2(5H)-FURANONES
    GRANDGUILLOT, JC
    ROUESSAC, F
    SYNTHESIS-STUTTGART, 1979, (08): : 607 - 609
  • [32] Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions
    Bellina, F
    Anselmi, C
    Rossi, R
    TETRAHEDRON LETTERS, 2001, 42 (23) : 3851 - 3854
  • [33] SYNTHESIS OF 3,4-DIARYL-2(5H)-FURANONES
    VIJAYARAGHAVAN, ST
    BALASUBRAMANIAN, TR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (07): : 760 - 761
  • [34] SYNTHESIS OF CHLORINATED 5-HYDROXY 4-METHYL-2(5H)-FURANONES AND MUCOCHLORIC ACID
    FRANZEN, R
    KRONBERG, L
    TETRAHEDRON LETTERS, 1995, 36 (22) : 3905 - 3908
  • [35] Facile approach to 4-substituted 2(5H)-furanones
    Yao, ML
    Deng, MZ
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16): : 5034 - 5036
  • [36] Mucochloric acid:: A useful synthon for the selective synthesis of 4-aryl-3chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidenel-3-chloro-2(5H)furanones and 3,4-diaryl-2(5H)-furanones
    Bellina, F
    Anselmi, C
    Martina, F
    Rossi, R
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) : 2290 - 2302
  • [37] Recent Progress in Metal-Catalyzed Reactions of 2(5H)-Furanones
    Mao, Chaoxu
    Wang, Zhaoyang
    Tan, Yuehe
    Xue, Fuling
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2011, 31 (09) : 1377 - 1387
  • [38] Preparation and reactions of 3,4-bisstannyl-2(5H)furanones
    Carter, NB
    Mabon, R
    Richecoeur, AME
    Sweeney, JB
    TETRAHEDRON, 2002, 58 (44) : 9117 - 9129
  • [39] SIMPLE PREPARATION OF 4-ARYL-2(5H)-FURANONES AND 4-ALKYL-2(5H)-FURANONES FROM BETA-SUBSTITUTED CROTONIC ESTERS
    KAGABU, S
    SHIMIZU, Y
    ITO, C
    MORIYA, K
    SYNTHESIS-STUTTGART, 1992, (09): : 830 - 832
  • [40] Synthesis of 5-arylamino-5-tert-butyl-5-hydroxy-2(5H)-furanones [1]
    Kozminykh, V.O.
    Bukanova, E.V.
    Belyaev, A.O.
    Kozminykh, E.N.
    Chemistry of Heterocyclic Compounds, 2003, Kluwer Academic/Plenum Publishers (39) : 1255 - 1256
12345