112221-07-5Relevant academic research and scientific papers
On the Reactivity of 4-Thioxo-2-azetidinones
Schaumann, Ernst,Moeller, Marianne
, p. 701 - 708 (2007/10/02)
Base-catalyzed alcoholysis of the N-S bond in N-sulfonyl-thioxoazetidinones 1 is a ready process; the resulting sulfonate then alkylates the liberated 2-.Alkylations of 2 under various conditions demonstrate that charge and thermodynamic control favor attack on nitrogen to give 5 rather than reaction on sulfur to give 4.Besides simple alkyl residues (4a-c, 5a-c) also fuctionalized alkyl (4d, e, g, m, n, o, 5d, e, g, i, m-o), aryl (5p), and acyl groups (5q) can be introduced and addition reactions (5r, s) achieved.Complex hydrides reduce the carbonyl group in 1, 5 to yield 8-10, but the C=N+ unit in the salt 6a to furnish β-lactam 11.Annulation of a five-membered ring to give 12 is achieved by 1,3-dipolar cycloaddition of dimethyl fumarate to in-situ generated azomethine ylide 6d.
