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- W2950879259 abstract "- The alkylation of 4-benzyl-2-phenyl-l,3-oxazol-5(4H)-one (11) with ω-azidoalkyl iodides (12) by deprotonation with LDA in THF/HMPT at -78 °C yielded mixtures of the 4,4-disubstituted 1,3-oxazol-5(4H)-ones (13) and the O-alkylated 1,3-oxazoles (14) in 65-50%, with 13 as the major product. The reaction of the latter with dimethylamine in acetonitrile at room temperature led to ω-azido-2-benzamido-2-benzylalkane amides (15), which were reduced to give the corresponding ω-amino derivatives (16). On treatment with HCl gas or BF 3 in boiling toluene, the macrocyclic 2-benzamido lactams (18) were formed in up to 27% yield via the intermediate formation of 1,3-oxazol-5(4H)-ones (17). The structures of the 14- and 15-membered lactams have been established by X-ray crystallography." @default.
- W2950879259 created "2019-06-27" @default.
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- W2950879259 date "2009-01-01" @default.
- W2950879259 modified "2023-10-06" @default.
- W2950879259 title "Synthesis of Macrocyclic Lactams from 2-(ω-Aminoalkyl)-2-benzoylamino-3-phenyl-N,N-dimethylpropanamides via Direct Amide Cyclization" @default.
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- W2950879259 doi "https://doi.org/10.3987/com-08-s(d)76" @default.
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