Synthesis of Oxindole-Appended Allyl Amines and Vinyl Aziridines via InCl₃/ArSH-Mediated Ring Opening of Vinyl Aziridines and Sulfur Ylide Aziridination

Abstract

A short and efficient synthesis of oxindole-appended allyl amines and 3-vinylaziridine-2-oxindoles have been accomplished in good yield via InCl₃/ArSH-mediated ring opening of 3-vinylaziridine-2-oxindoles and sulfur ylide aziridination, respectively. The sulfur ylide was generated in situ from the bromo isomerized Morita–Baylis–Hillman adduct of isatin with N-tosyl imines and tetrahydrothiophene under basic conditions.

Key words

heterocycles - oxindole - ring opening - ylides - cyclization

• References and Notes

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