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Paper | Regular issue | Vol 31, No. 1, 1990, pp.173-186
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5240
Synthesis and Reactivity of 2-(1,3-Dithian-2-yl)indoles. III. Influence of the Indole Protective N-Phenylsulfonyl Group

Mario Rubiralta,* Anna Diez, Ignashi Reig, Josep Castells, Jean-Luc Bettiol, David S. Grierson, and Henri-Philippe Husson

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain

Abstract

Formation of the anion 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.