Syntheses of Substituted
Furans and Pyrroles by Platinum-Catalyzed Cyclizations
of Propargylic Oxiranes and Aziridines in Aqueous Media

Masahiro Yoshida; Mohammad Al-Amin; Kozo Shishido

doi:10.1055/s-0029-1216867

FEATUREARTICLE

Syntheses of Substituted Furans and Pyrroles by Platinum-Catalyzed Cyclizations of Propargylic Oxiranes and Aziridines in Aqueous Media

Masahiro Yoshida*, Mohammad Al-Amin, Kozo Shishido
Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan
Fax: +81(88)6337294; e-Mail: yoshida@ph.tokushima-u.ac.jp;

Abstract

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Abstract

The reactions of propargylic oxiranes and aziridines with a platinum catalyst in aqueous media are described. Furans having a variety of substituents were conveniently synthesized by the platinum-catalyzed reaction of propargylic oxiranes. The reaction in the presence of N-iodosuccinimide afforded the 3-iodo-substituted furan, which was further functionalized to tetrasubstituted furans with high efficiency. Propargylic aziridines were also reacted with the platinum catalyst to produce the corresponding substituted pyrroles in good yields.

Key words

alkyne - epoxide - furan - platinum - pyrrole

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References

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