Novel intramolecular reactivity of oximes: synthesis of cyclic and spiro-fused imines |
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Authors: | Savarin Cécile G Grisé Christiane Murry Jerry A Reamer Robert A Hughes David L |
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Affiliation: | Department of Process Research, Merck Research Laboratories, Merck & Co., P.O. Box 2000, Rahway, NJ 07065, USA. cecilesavarin@gmail.com |
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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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