Mononuclear isoheterocyclic rearrangements. Note I. Interconversion of 3-benzoylamino-5-methyl-1,2,4-oxadiazole and 3-acetylamino-5-phenyl-1,2,4-oxadiazole

Autor:	Nicolò Vivona, Domenico Spinelli, Giuseppe Cusmano, Michele Ruccia
Rok vydání:	1975
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Acetone Oxadiazole Organic chemistry Reversible process Methanol Medicinal chemistry
Zdroj:	Journal of Heterocyclic Chemistry. 12:985-988
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570120533
Popis:	The first example of mononuclear isoheterocyclic rearrangement is reported. The 3-benzoylamino-5-methyl-1,2,4-oxadiazole (5) furnishes through a reversible process (slowly at room temperature in methanol, acetone or dioxane, fast in DMSO or in methanol in the presence of strong bases) a mixture of 5 and 3-acethylamino-5-phenyl-1,2,4-oxadiazole (6). The equilibrium process can be achieved also by heating 5 at 181° and the same reaction mixture can be obtained using 6 as the starting material. 3-Trichloroacetylamino-5-methyl-1,2,4-oxadiazole (7) was unaffected by similar treatment. The results obtained are discussed.
Databáze:	OpenAIRE
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