Reactions of salicyl N-tosylimines or salicylaldehydes with diethyl acetylenedicarboxylate for the synthesis of highly functionalized chromenes

被引:47
作者
Guo, Ying-Wen
Shi, Yong-Ling
Li, Hong-Bin
Shi, Min
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
[2] Shanghai Univ, Sch Environm & Chem Engn, Shanghai 201800, Peoples R China
基金
中国国家自然科学基金;
关键词
salicyl N-tosylimines; salicylaldehydes; DABCO; PPhMe2; diethyl acetylenedicarboxylate; chromenes;
D O I
10.1016/j.tet.2006.04.011
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Reactions of diethyl acetylenedicarboxylate with salicyl N-tosylimines or salicylaldehydes proceeded smoothly in the presence of DABCO or dimethylphenylphosphine under mild conditions to give the corresponding chromenes in excellent yields. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5875 / 5882
页数:8
相关论文
共 27 条
[1]
DISCOVERY OF INSECT ANTI-JUVENILE HORMONES IN PLANTS [J].
BOWERS, WS ;
OHTA, T ;
CLEERE, JS ;
MARSELLA, PA .
SCIENCE, 1976, 193 (4253) :542-547
[2]
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
[3]
Bifunctional activation and racemization in the catalytic asymmetric aza-Baylis-Hillman reaction [J].
Buskens, P ;
Klankermayer, J ;
Leitner, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :16762-16763
[4]
Ellis G.P., 1977, Chromenes, chromanones, and chromones, DOI 10.1002/9780470187012
[5]
REACTIONS OF DIMETHYL ACETYLENEDICARBOXYLATE .10. REACTION WITH SALICYLALDEHYDE, ORTHO HYDROXYACETOPHENONE, 2-HYDROXYCHALCONES AND 2,2'-DIHYDROXYCHALCONES [J].
GUPTA, RK ;
GEORGE, MV .
TETRAHEDRON, 1975, 31 (10) :1263-1275
[6]
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
[7]
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
[8]
Kaye PT, 2003, SYNTHESIS-STUTTGART, P531
[9]
Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay.: 1.: Structure-activity relationships of the 4-aryl group [J].
Kemnitzer, W ;
Drewe, J ;
Jiang, SC ;
Zhang, H ;
Wang, Y ;
Zhao, JH ;
Jia, SJ ;
Herich, J ;
Labreque, D ;
Storer, R ;
Meerovitch, K ;
Bouffard, D ;
Rej, R ;
Denis, R ;
Blais, C ;
Lamothe, S ;
Attardo, G ;
Gourdeau, H ;
Tseng, B ;
Kasibhatla, S ;
Cai, SX .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) :6299-6310
[10]
Base-catalyzed condensation of 2-hydroxybenzaldehydes with α,β-unsaturated aldehydes -: Scope and limitations [J].
Lesch, B ;
Toräng, J ;
Vanderheiden, S ;
Bräse, S .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :555-562