On the reactivity of nitrosoimidazoles with acids (the Cusmano–Ruccia reaction): a continuous source of new ring-into-ring interconversion

Abstract An extension of the ‘Cusmano–Ruccia’ reaction is reported. 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1- b ]oxazole by the action of hydrochloric acid gives 3-(4-chlorobenzoyl)-5-methyl-1,2,4-oxadiazole ( 13 ); presumably via ammonium ion, CO 2 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 interconversion has been once more confirmed.