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Synthesis and Reactions of Some 1-Substituted 1,2-Diazetidinones
Taylor, Edward C.,Davies, Huw M. L.
, p. 4415 - 4419 (2007/10/02)
A number of 1,2-diazetidin-3-ones variously substituted at N-1 have been prepared by sodium borohydride reduction of, or addition of methylmagnesium bromide to, 3-oxo-1,2-diazetidinium inner salts (formed by condensation of 3-oxo-1,2-diazetidinium tosylate with carbonyl compounds). 1-Cinnamyl-1,2-diazetidin-3-ones, silylated at N-2, underwent base-promoted alkylation and aldol reactions at C-4.Some unusual dimerization and fragmentation reactions of these aza-β-lactam derivatives have been observed.
