93847-35-9Relevant academic research and scientific papers
Synthesis and ring transformations of 1,2,5-oxadiazinan-3,6-diones
Geffken, Detlef,Von Zydowitz, Hans,Ploetz, Alf
, p. 967 - 972 (2007/10/03)
1,2,5-Oxadiazinan-3,6-diones (8), easily available by cyclic carbonylation of α-amino-carbohydroxamic acids 7 with 1,1-carbonyldiimidazole, are reacted with hydrazine to give 3-aminohydantoins (10). Depending on the substituents R1TR' 8 was fou
Synthesis of 1,2-Diazetidinones (Aza-β-lactams) by Photochemical Ring Contraction
Lawton, Geoffrey,Moody, Christopher J.,Pearson, Christopher J.
, p. 877 - 884 (2007/10/02)
Irradiation of 4-diazopyrazolidine-3,5-diones (11) in the presence of alcohols, diethylamine, or water gives 1,2-diazetidinones (12) formed by photochemical Wolff rearrangement with ring contraction followed by reaction of the resulting ketene with the nucleophile.In the case of the bicyclic diazo compound (11d) a fragmentation reaction competes with ring contraction.The aza-β-lactams (12) show the expected high frequency carbonyl stretch in their i.r. spectra.The acid (12e) readily decarboxylates to give the 4-unsubstituted 1,2-dibenzyldiazetidinone (28), the four-membered ring of which is cleaved by alkaline hydrolysis, lithium aluminium hydride or diborane to give (29), (30), and (31), respectively (Scheme 9).Attempts to modify the carboxy substituent of (12e) into an acylamino group were unsuccessful.
Synthesis of Aza-β-lactams by Photochemical Ring Contraction
Lawton, Geoffrey,Moody, Christopher J.,Pearson, Christopher J.
, p. 754 - 756 (2007/10/02)
Photochemical decomposition of 4-diazopyrazolidine-3,5-diones (3) in the presence of nucleophiles, XH, leads to the aza-β-lactams (4); decarboxylation of (4e) gives the aza-β-lactam (7), which undergoes reductive ring cleavage to (8), and ring expansion to (9) on treatment with base.
