PHOTOCYCLOADDITION OF QUINOXALINE-2(1H)-THIONES TO ALKENES

被引:12
作者
NISHIO, T
机构
[1] Department of Chemistry, University of Tsukuba, Tsukuba-Shi, Ibaraki
关键词
D O I
10.1002/hlca.19920750208
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A synthetically useful C-C bond formation involving the photochemical addition of quinoxaline-2(1H)-thiones to alkenes is described. Irradiation of the quinoxaline-2(1H)-thiones 1-4 in the presence of the alkenes 7 gave the 2-(2'-mercaptoalkyl)quinoxalines 8-11 in moderate-to-good yields via ring cleavage of an intermediate aminothietane with aromatization of the quinoxaline ring. The latter was formed by [2 + 2] photocycloaddition of the C = S bond of the quinoxaline-2(1H)-thione and the C = C bond of the alkene.
引用
收藏
页码:487 / 492
页数:6
相关论文
共 31 条
[1]   SYNTHESIS AND REACTIONS OF QUINOXALINE DERIVATIVES [J].
BADR, MZA ;
ELNAGGAR, GM ;
ELSHERIEF, HAH ;
MAHGOUB, SA .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (06) :1653-1657
[2]   THIOENAMIDE PHOTOCHEMISTRY [J].
COUTURE, A ;
DUBIEZ, R ;
LABLACHECOMBIER, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (15) :842-843
[3]   SECONDARY ENAMIDE AND THIOENAMIDE PHOTOCHEMISTRY - A NEW SPIROANNELATION METHOD [J].
COUTURE, A ;
DUBIEZ, R ;
LABLACHECOMBIER, A .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (04) :714-717
[4]   PHOTOCYCLOADDITION REACTIONS OF N-METHYLTHIOPHTHALIMIDE [J].
COYLE, JD ;
RAPLEY, PA .
TETRAHEDRON LETTERS, 1984, 25 (21) :2247-2248
[5]   PHOTOCHEMICAL CYCLOADDITION REACTIONS OF N-METHYL(THIOPHTHALIMIDE) AND N-METHYL(DITHIOPHTHALIMIDE) WITH ALKENES [J].
COYLE, JD ;
RAPLEY, PA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2273-2278
[6]   PHOTOCHEMISTRY OF ORGANIC SULFUR-COMPOUNDS [J].
COYLE, JD .
CHEMICAL SOCIETY REVIEWS, 1975, 4 (04) :523-532
[7]  
COYLE JD, 1985, TETRAHEDRON, V41, P5395
[8]  
DAS BC, 1978, J CHEM RES-S, P370
[9]  
DEMAYO P, 1980, J ORG CHEM, V45, P1549, DOI 10.1021/jo01297a001
[10]   PHOTOCHEMICAL-SYNTHESIS .62. THIONE PHOTOCHEMISTRY, AND CHEMISTRY OF S2 STATE [J].
DEMAYO, P .
ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (02) :52-59