51807-79-5Relevant academic research and scientific papers
On the reactivity of nitrosoimidazoles with acids (the Cusmano-Ruccia reaction): A continuous source of new ring-into-ring interconversion
Cosimelli, Barbara,Frenna, Vincenzo,Rambaldi, Mirella,Severi, Elda,Spinelli, Domenico
, p. 1488 - 1490 (2014/03/21)
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, 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 interconversion has been once more confirmed.
Ring-ring interconversions of nitrosoimidazoles. The effect of some condensed six-membered rings on the reactivity
Billi,Cosimelli,Spinelli,Andreani,Leoni
, p. 6527 - 6532 (2007/10/03)
The study of the effect of a condensed ring on the reactivity of nitrosoimidazoles with hydrochloric acid has been extended to some six-membered rings: thus, the reactivity of 2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-a]pyridine (6), 6-chloro-2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-b]pyridazine (7), 2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-a]pyrimidine (8a) and 2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-a]pyrazine (9) has been examined. The striking differences observed in the reactivity of compounds 6-9 (denitrosation, ring-opening with ammonia elimination, ring-ring interconversion with the unexpected loss of a C3 fragment and decomposition, respectively) have been discussed. (C) 2000 Elsevier Science Ltd.
