4.6 Article

N-Allylation versus C-allylation of intermediates from aza-Michael adducts of arylideneisoxazol-5-ones

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 18, 期 46, 页码 9516-9525

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01998d

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  1. Ministry of Science and Technology, Taiwan [MOST107-2113-M002-005]

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Reactions of arylidene-isoxazol-5-ones with intermediates from palladium-catalysed decarboxylation of allyl carbamates proceeded through aza-Michael addition and N-allylation to give the corresponding bis-adducts, beta -amido-N-allylated products, in good yields. In similar reactions with 4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-one, a cyclic allyl carbamate, C-allylation took place to yield a series of spiro[isoxazole-4,3 ' -quinolin]-5-ones in high yields. Regio-selective N- versus C-allylation is illustrated to occur in an inter- versus intra-molecular fashion. The structure and stereochemistry of these products are determined by NMR spectroscopy and further confirmed by X-ray crystallography. This work offers an excellent method for the preparation of various substituted isoxazol-5-ones.

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