Synthesis of Tetrahydrofuro[2,3-d]oxazoles and Oxazoles by Hypervalent Iodine (III)-Promoted [2 + 2 + 1] Annulation

Hiroaki Ishida; Shoya Homma; Ryota Kasuga; Keiko Yamamoto; Toshimasa Itoh

doi:10.1248/cpb.c21-01001

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Synthesis of Tetrahydrofuro[2,3-d]oxazoles and Oxazoles by Hypervalent Iodine (III)-Promoted [2 + 2 + 1] Annulation

Hiroaki Ishida , Shoya Homma, Ryota Kasuga, Keiko Yamamoto, Toshimasa Itoh

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Keywords: hypervalent iodine, [2 + 2 + 1] annulation, tetrahydrofuro[2,3-d]oxazole, oxazole

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Supplementary material

2022 Volume 70 Issue 3 Pages 192-194

DOI https://doi.org/10.1248/cpb.c21-01001

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Abstract

Reaction of a hypervalent iodine reagent with bistriflimide efficiently promotes three-component regioselective cyclization of tetrahydrofuro[2,3-d]oxazoles and oxazoles from homopropargyl alcohols bearing a phenyl group, with different substituents on the aryl alkyne compounds affecting the selectivity of the resulting product. Utilizing the hydroxyethyl oxazole derivatives obtained in this research could aid in the development of various peroxisome proliferator-activated receptor agonist derivatives.

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