Pyrrolizine-1,3-dione.
نویسندگان
چکیده
Pyrrolizine-1,3-dione 4 was made by oxidation of the alcohol 2 using pyridinium chlorochromate. The dione 4 shows ketone properties (e.g. formation of DNP derivative 11) and, in common with other pyrrolizinones, the lactam unit is readily ring-opened by methanol under basic conditions. The active methylene unit of 4 couples readily with diazonium salts to provide the hydrazone 15 whose structure was confirmed by X-ray crystallography. The 'Meldrumsated' derivative 18 exists exclusively as the tautomer 18F; flash vacuum pyrolysis (FVP) of 18 at 700 degrees C gives the pyronopyrrolizine 20 exclusively. Reaction of 4 with DMF acetal gives the dimethylaminomethylene derivative 22 which exists as a mixture of rotamers at room temperature.
منابع مشابه
1′-(2-Chlorophenyl)-5,6,5′,6′,7′,7a′-hexahydro-1′H,1′′H-dispiro[imidazo[2,1-b][1,3]thiazole-2,2′-pyrrolizine-3′(2′H),3′′-indole]-2′′,3(2H,3′′H)-dione
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The IR and NMR spectra were coupled with quantum chemical calculations in DFT approach usingthe hybrid B3LYP exchange-correlation functional to confirm the structure of 2-methoxycarbonyl-7-methyl-1,3-thiazino[3,2-b][1,2,4]triazine-4,8-dione 2d.
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 8 19 شماره
صفحات -
تاریخ انتشار 2010