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Paper | Regular issue | Vol 34, No. 9, 1992, pp.1737-1748
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6067
Synthesis of Selenopsilocine (3-Dimethylaminoethyl-4-hydroxybenzo[b]selenophene)

Abdelmjid Dari, Léon E. Christiaens, and Marcel J. Renson*

*Heterocyclic Chemistry, Institute of Organic Chemistry, B.6., University of Liège, Sart-Tilman, 4000 LIEGE, Belgium

Abstract

Starting from the known 6-methoxyanthranilic acid (5), we have synthesized in six steps the selenium analogue of psilocine (1c). The key intermediate is the 4-methoxyselenoindoxyl (8), which is condensed with the dimethylaminocarbamoylmethylenetriphenylphosphorane to give the aromatic amide (9a). Its reduction with lithium aluminium hydride leads to the methoxyamine (9b) which is finally demethylated by sodium ethanethiolate to 1c.