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
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 [J].
Agami, C ;
Dechoux, L ;
Ménard, C ;
Hebbe, S .
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 [J].
Agami, C ;
Amiot, F ;
Couty, F ;
Dechoux, L .
TETRAHEDRON LETTERS, 1998, 39 (30) :5373-5374
[6]   Enantioselective synthesis of β-amino-diacids [J].
Alladoum, J ;
Dechoux, L .
TETRAHEDRON LETTERS, 2005, 46 (47) :8203-8205
[7]   Aza-annulation of β-enaminolactones: application to the synthesis of enantiopure difunctionalized bicyclic lactams [J].
Alladourn, Jeanne ;
Toum, Valerie ;
Hebbe, Severine ;
Kadouri-Puchot, Catherine ;
Dechoux, Luc .
TETRAHEDRON LETTERS, 2009, 50 (06) :617-619
[8]   Stereoselective synthesis of functionalized butenolides by the photochemical rearrangement of [2,1]benzisoxazolequinone derivatives. [J].
Armesto, D ;
RodriguezMorgade, S ;
Ortiz, MJ ;
Vazquez, P ;
Torres, T .
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 [J].
Augustine, John Kallikat ;
Naik, Yanjerappa Arthoba ;
Mandal, Ashis Baran ;
Chowdappa, Nagaraja ;
Praveen, Vinuthan B. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9854-9856
[10]   gem-Dibromomethyl Aromatics: Efficient Aldehyde Equivalents in the Knoevenagel-Doebner Reaction [J].
Augustine, John Kallikat ;
Naik, Yanjerappa Arthoba ;
Poojari, Subba ;
Chowdappa, Nagaraja ;
Sherigara, Bailur Sheena ;
Areppa, Kummara .
SYNTHESIS-STUTTGART, 2009, (14) :2349-2356