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, 9 (6), 981-3

Novel Intramolecular Reactivity of Oximes: Synthesis of Cyclic and Spiro-Fused Imines

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Novel Intramolecular Reactivity of Oximes: Synthesis of Cyclic and Spiro-Fused Imines

Cécile G Savarin et al. Org Lett.

Abstract

Under conventional heat (135-145 degrees C) or microwave irradiation and 1 equiv of acetic anhydride, ortho-substituted aryl-oximes undergo a novel sp3 C-H activated cyclization to produce the corresponding isoindoles, and aliphatic oximes afford the corresponding dihydropyrroles. The cyclization occurs with various substrates in good yield (46-82%) leading to unique spiro-fused and cyclic imines. An initial mechanistic investigation suggests the reaction occurs via a nitrenium or vinyl nitrene intermediate. [reaction: see text]

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