An extension of the ‘Cusmano–Ruccia’ reaction is reported. 6-(4-chlorophenyl)-3-methyl-5-nitrosoimi-dazo[2,1-b]oxazole by the action of hydrochloric acid gives 3-(4-chlorobenzoyl)-5-methyl-1,2,4-oxadiaz-ole (13); presumably via ammonium ion, CO2 and methanol elimination. The relevance of the nature of the atom of the B-ring linked to C-2 of the imidazole for the occurrence of the ring-into-ring interconver-sion has been once more confirmed.
Cosimelli, B., Frenna, V., Rambaldi, M., Severi, E., Spinelli, D. (2014). On the reactivity of nitrosoimidazoles with acids (the Cusmano-Ruccia reaction): a continuous source of new ring- into-ring interconversion. TETRAHEDRON LETTERS, 55, 1488-1490 [10.1016/j.tetlet.2014.01.060].
On the reactivity of nitrosoimidazoles with acids (the Cusmano-Ruccia reaction): a continuous source of new ring- into-ring interconversion
FRENNA, Vincenzo;
2014-01-01
Abstract
An extension of the ‘Cusmano–Ruccia’ reaction is reported. 6-(4-chlorophenyl)-3-methyl-5-nitrosoimi-dazo[2,1-b]oxazole by the action of hydrochloric acid gives 3-(4-chlorobenzoyl)-5-methyl-1,2,4-oxadiaz-ole (13); presumably via ammonium ion, CO2 and methanol elimination. The relevance of the nature of the atom of the B-ring linked to C-2 of the imidazole for the occurrence of the ring-into-ring interconver-sion has been once more confirmed.
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