Synthesis of substituted 3,4-dihydroquinolin-2(1H)-one derivatives by sequential Ugi/acrylanilide [6π]-photocyclizations

被引:20
作者
Akritopoulou-Zanze, Irini [1 ]
Whitehead, Alan [1 ]
Waters, Jan E. [1 ]
Henry, Rodger F. [1 ]
Djuric, Stevan W. [1 ]
机构
[1] Abbott Labs, Scaffold Oriented Synth & Struct Chem, Abbott Pk, IL 60064 USA
关键词
D O I
10.1016/j.tetlet.2007.03.099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the synthesis of highly functionalized 3,4-dihydroquinolin-2(1H)-ones via sequential Ugi/acrylanilide photocyclization reactions. The [6 pi]-photocyclization proceeds in excellent yields and with preferential trans-selectivity for the newly formed ring system. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3549 / 3552
页数:4
相关论文
共 16 条
[1]   Synthesis of novel and uniquely shaped 3-azabicyclo[4.2.0]octan-4-one derivatives by sequential Ugi/[2+2] ene-enone photocycloadditions [J].
Akritopoulou-Zanze, Irini ;
Whitehead, Alan ;
Waters, Jan E. ;
Henry, Rodger F. ;
Djuric, Stevan W. .
ORGANIC LETTERS, 2007, 9 (07) :1299-1302
[2]   Enantioselective [6π]-photocyclization reaction of an acrylanilide mediated by a chiral host.: Interplay between enantioselective ring closure and enantioselective protonation [J].
Bach, T ;
Grosch, B ;
Strassner, T ;
Herdtweck, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :1107-1116
[3]   STRUCTURE OF MELODINUS ALKALOIDS, (+)-MELOSCINE,(+)-EPIMELOSCINE AND (+)-SCANDINE .1. ALKALOIDS FROM MELODINUS SCANDENS FORST [J].
BERNAUER, K ;
ENGLERT, G ;
VETTER, W ;
WEISS, E .
HELVETICA CHIMICA ACTA, 1969, 52 (07) :1886-&
[4]  
Cabezas F, 2003, CHEM PHARM BULL, V51, P315
[5]   PHOTOISOMERIZATION OF SUBSTITUTED ACRYLIC ACIDS AND ACRYLAMIDES TO BETA-LACTONES AND BETA-LACTAMS [J].
CHAPMAN, OL ;
ADAMS, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (09) :2333-&
[6]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[7]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[8]  
2-U
[9]   THE STRUCTURE OF THE CALABASH CURARE ALKALOID CALEBASSINE-1 .183. NATURALLY-OCCURRING ORGANIC-SUBSTANCES [J].
GUGGISBERG, A ;
PREWO, R ;
BIERI, JH ;
HESSE, M .
HELVETICA CHIMICA ACTA, 1982, 65 (08) :2587-2597
[10]   Multi-component reactions : Emerging chemistry in drug discovery 'From xylocain to crixivan' [J].
Hulme, C ;
Gore, V .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (01) :51-80