SYNTHESIS AND REACTIVITY OF 2-(1,3-DITHIAN-2-YL)INDOLES .3. INFLUENCE OF THE INDOLE PROTECTIVE N-PHENYLSULFONYL GROUP

被引:22
作者
RUBIRALTA, M [1 ]
DIEZ, A [1 ]
REIG, I [1 ]
CASTELLS, J [1 ]
BETTIOL, JL [1 ]
GRIERSON, DS [1 ]
HUSSON, HP [1 ]
机构
[1] CNRS,INST CHIM SUBST NAT,F-91190 GIF SUR YVETTE,FRANCE
关键词
D O I
10.3987/COM-89-5240
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Formation of the anion of 2-(1,3-dithian-2-yl)indoles was shown to be possible when the indole nitrogen is protected by a p-methoxyphenylsulfonyl group. In contrast to the corresponding N-phenylsulfonylindole dithiane 1, the anion of dithiane 2 reacts efficiently with electrophiles.The influence of the indole protective group on the metallation of 2-bis(ethylthio)-methyl-1-(phenylsulfonyl)indole (14) and the corresponding sulfoxide 24 with n-butyllithium is also reported. © 1990.
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页码:173 / 186
页数:14
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