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Synthesis 2003(8): 1191-1200
DOI: 10.1055/s-2003-39401
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Triflic Anhydride-Promoted Cyclization of Sulfides: A Convenient Synthesis of Fused Sulfur Heterocycles

Nikolay E. Shevchenko, Valentine G. Nenajdenko*, Elizabeth S. Balenkova
Department of Chemistry, Moscow State University, Moscow, 119992, Russia
Fax: +7(095)9328846; e-Mail: nen@acylium.chem.msu.ru;
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Publikationsverlauf

Received 6 March 2003
Publikationsdatum:
26. Mai 2003 (online)

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Abstract

A new approach to the synthesis of annulated sulfur heterocycles based on triflic anhydride-promoted cyclization of the hetaryl(aryl) containing alkyl sulfides was elaborated. Smooth de­methylation of initially formed cyclic sulfonium salts by treatment with triethylamine afforded a number of five-, six- and seven-membered fused sulfur heterocycles. Unexpected ring opening took place in the reaction of diethylamine with 5-membered sulfonium salts.

Key words

cyclizations - electrophilic aromatic substitutions - sulfur heterocycles - bicyclic compounds - sulfonylsulfonium salts

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