Synthesis of substituted chromenes through the DABCO-catalyzed reaction of but-3-yn-2-one and methyl propiolate with salicyl N-tosylimines (DABCO=1,4-diazabicyclo [2.2.2] octane)

被引:43
作者
Shi, YL [1 ]
Shi, M [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
Baylis-Hillman reaction; chromenes; Michael addition; NMR spectroscopy; salicyl n-tosylimines;
D O I
10.1002/chem.200501291
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The DABCO-catalyzed (DAB CO = 1 4-diazabicyclo [2.2.2]octane) reaction of but-3-yn-2-one and methyl propiolate with salicyl N-tosylimines yields nal mechanism for the reaction has been demonstrated on the basis of H-1 NMR spectroscopic investigation.
引用
收藏
页码:3374 / 3378
页数:5
相关论文
共 29 条
[1]  
Aggarwal V. K., 2005, ANGEW CHEM, V117, P1734
[2]   Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis [J].
Aggarwal, VK ;
Fulford, SY ;
Lloyd-Jones, GC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1706-1708
[3]  
[Anonymous], 2004, ANGEW CHEM, DOI DOI 10.1002/ANGE.200460059
[4]   DISCOVERY OF INSECT ANTI-JUVENILE HORMONES IN PLANTS [J].
BOWERS, WS ;
OHTA, T ;
CLEERE, JS ;
MARSELLA, PA .
SCIENCE, 1976, 193 (4253) :542-547
[5]   Novel heteroarotinoids as potential antagonists of Mycobacterium bovis BCG [J].
Brown, CW ;
Liu, SQ ;
Klucik, J ;
Berlin, KD ;
Brennan, PJ ;
Kaur, D ;
Benbrook, DM .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (04) :1008-1017
[6]  
Ellis G.P., 1977, Chromenes, chromanones, and chromones, DOI 10.1002/9780470187012
[7]   Racemic and asymmetric Diels-Alder reactions of 1-(2-oxazolidinon-3-yl)-3-siloxy-1,3-butadienes [J].
Janey, JM ;
Iwama, T ;
Kozmin, SA ;
Rawal, VH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9059-9068
[8]   A NEW PREPARATIVE METHOD OF 2,2-DIMETHYL-H-2-CHROMENES [J].
KAWASE, Y ;
YAMAGUCHI, S ;
HORITA, H ;
TAKENO, J ;
KAMEYAMA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (04) :1153-1155
[9]   Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis-Hillman pathway? [J].
Kaye, PT ;
Musa, MA ;
Nocanda, XW ;
Robinson, RS .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (07) :1133-1138
[10]  
Kaye PT, 2003, SYNTHESIS-STUTTGART, P531