Electron deficient dienes 3: Rapid access to 2-hydroxybenzophenones via inverse electron demand Diels-Alder-driven domino reactions of a chromone-fused electron deficient diene with enamines

被引:30
作者
Bodwell, GJ [1 ]
Hawco, KM [1 ]
da Silva, RP [1 ]
机构
[1] Mem Univ Newfoundland, Dept Chem, St Johns, NF A1B 3X7, Canada
关键词
domino reactions; inverse electron demand Diels-Alder; chromones; enamines; benzophenones;
D O I
10.1055/s-2003-36800
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Horner-Wadsworth-Emnions reaction of 3-formyl-chromone affords an electron deficient 1,3-diene that undergoes domino inverse electron demand Diels-Alder/elimination/intramolecular elimination reactions with enamines to afford functionalized 2-hydroxybenzophenones.
引用
收藏
页码:179 / 182
页数:4
相关论文
共 56 条
[1]   DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].
AFARINKIA, K ;
VINADER, V ;
NELSON, TD ;
POSNER, GH .
TETRAHEDRON, 1992, 48 (42) :9111-9171
[2]   XANTHONES FROM GUTTIFERAE [J].
BENNETT, GJ ;
LEE, HH .
PHYTOCHEMISTRY, 1989, 28 (04) :967-998
[3]   Laser flash photolysis studies on the monohydroxy derivatives of benzophenone [J].
Bhasikuttan, AC ;
Singh, AK ;
Palit, DK ;
Sapre, AV ;
Mittal, JP .
JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (20) :3470-3480
[4]  
Bodwell GJ, 2002, ANGEW CHEM INT EDIT, V41, P3261, DOI 10.1002/1521-3773(20020902)41:17<3261::AID-ANIE3261>3.0.CO
[5]  
2-K
[6]   Electron deficient dienes .1. Normal and inverse electron demand Diels-Alder reactions of the same carbon skeleton. [J].
Bodwell, GJ ;
Pi, ZL .
TETRAHEDRON LETTERS, 1997, 38 (03) :309-312
[7]  
Bodwell GJ, 1999, SYNLETT, P477
[8]  
BOGER DL, 1990, B SOC CHIM BELG, V99, P599
[9]   Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine [J].
Boger, DL ;
Wolkenberg, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9120-9124
[10]   DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].
BOGER, DL .
CHEMICAL REVIEWS, 1986, 86 (05) :781-793