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- W3093473065 abstract "A new and efficient method for the synthesis of 6-chloro-substituted 2-methylene-2,3-dihydro-1,4-oxazepines has been demonstrated. Upon treatment with N-chlorosuccinimide in acetonitrile, N-propargylic β-enaminones underwent chlorination to afford α-chlorinated N-propargylic β-enaminones, which was then subjected to electrophilic cyclization with zinc chloride in refluxing chloroform to yield 6-chloro-2-methylene-2,3-dihydro-1,4-oxazepines. It was shown for the first time that on N-propargylic β-enaminone systems, α-chlorination exclusively preponderates over the formation of chloronium ion. The method was found to be general for a diversity of N-propargylic β-enaminones and tolerated the presence of a wide range of aryl, heteroaryl and alkyl groups with electron-donating and electron-withdrawing substituents. The method was also applicable as the one-pot two-step process without isolating the intermediate α-chlorinated N-propargylic β-enaminones. This operationally easy method may provide a rapid entry to a library of highly functionalized 6-chloro-2-methylene-2,3-dihydro-1,4-oxazepines with potential medicinal applications for human health." @default.
- W3093473065 created "2020-10-22" @default.
- W3093473065 creator A5042135738 @default.
- W3093473065 creator A5063787840 @default.
- W3093473065 date "2020-11-01" @default.
- W3093473065 modified "2023-09-26" @default.
- W3093473065 title "A facile synthesis of 6-chloro-2-methylene-2,3-dihydro-1,4-oxazepines from N-propargylic β-enaminones" @default.
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- W3093473065 doi "https://doi.org/10.1016/j.tet.2020.131650" @default.
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