Alkaline salt-catalyzed aza Diels-Alder reactions of Danishefsky's diene with imines in water under neutral conditions

被引:57
作者
Loncaric, C [1 ]
Manabe, K [1 ]
Kobayashi, S [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1039/b300880k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two- or three-component aza Diels-Alder reactions of Danishefsky's diene with imines or aldehydes and amines in water took place smoothly under neutral conditions in the presence of a catalytic amount of an alkaline salt such as sodium triflate to afford dihydro-4-pyridones in high yields.
引用
收藏
页码:574 / 575
页数:2
相关论文
共 27 条
[1]  
Akiyama T, 2002, SYNLETT, P1898
[2]   Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media [J].
Akiyama, T ;
Takaya, J ;
Kagoshima, H .
TETRAHEDRON LETTERS, 1999, 40 (44) :7831-7834
[3]   Indium triflate - An efficient catalyst for hetero Diels-Alder reactions [J].
Ali, T ;
Chauhan, KK ;
Frost, CG .
TETRAHEDRON LETTERS, 1999, 40 (30) :5621-5624
[4]   Imino-Diels-Alder and imino-aldol reactions catalyzed by samarium diiodide [J].
Collin, J ;
Jaber, N ;
Lannou, MI .
TETRAHEDRON LETTERS, 2001, 42 (42) :7405-7407
[5]   USEFUL DIENE FOR DIELS-ALDER REACTION [J].
DANISHEFSKY, S ;
KITAHARA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7807-7808
[6]  
Fringuelli F, 2001, EUR J ORG CHEM, V2001, P439, DOI 10.1002/1099-0690(200102)2001:3<439::AID-EJOC439>3.0.CO
[7]  
2-B
[8]  
Grieco P.A., 1998, Organic synthesis in water
[9]  
JORGENSEN KA, 2002, ANGEW CHEM INT EDIT, V39, P3558
[10]  
KOBAYASHI S, 1994, SYNLETT, P689