Wan S.-HLi X.-ALiu Y.-HSHIUH-TZUNG LIU2021-08-032021-08-03202014770520https://www.scopus.com/inward/record.uri?eid=2-s2.0-85097417967&doi=10.1039%2fd0ob01998d&partnerID=40&md5=49c0184f6419fa17cf4b90789919dda7https://scholars.lib.ntu.edu.tw/handle/123456789/575874Reactions 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, β-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. This journal is ? The Royal Society of Chemistry.Addition reactions; Carboxylation; Nuclear magnetic resonance spectroscopy; Reaction intermediates; X ray crystallography; Aza-Michael addition; Bis-adducts; High yield; Isoxazoles; Michael adducts; Regio-selective; Allylation; allylation; article; nuclear magnetic resonance spectroscopy; stereochemistry; X ray crystallographyjournal article10.1039/d0ob01998d331886672-s2.0-85097417967