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

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

References

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Hashmi also reported the conversion of 1i using a gold catalyst, in which the reaction was complete in 17 h affording 2i in 80% yield; see ref 4h.