The Journal of organic chemistry

Regiochemical switching in Diels-Alder cycloadditions by change in oxidation state of removable diene sulfur substituents. Synthesis of carbazoles by sequential …

TG Back, A Pandyra, JE Wulff

Index: Back, Thomas G.; Pandyra, Aleksandra; Wulff, Jeremy E. Journal of Organic Chemistry, 2003 , vol. 68, # 8 p. 3299 - 3302

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Citation Number: 29

Abstract

The palladium-catalyzed heteroannulation of N-carbobenzyloxy-o-iodoanilines with 1- phenylthio-1, 3-butadiene afforded indolines 7, which were oxidized with DDQ to produce vinylogous 2-(phenylthio) indoles 8. The latter compounds underwent highly regioselective Diels-Alder cycloadditions with methyl propiolate in the presence of MeAlCl2 or AlCl3, with simultaneous elimination of benzenethiol, to afford methyl N-(carbobenzyloxy) carbazole- ...

~89%

~17%

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