Mass spectrometry of 1,2,5-oxadiazole N-oxide derivatives: use of deuterated analogues in fragmentation pattern studies

• Autor(a) principal: Cerecetto,Hugo
• Data de Publicação: 2004
• Outros Autores: González,Mercedes, Seoane,Gustavo, Stanko,Carola, Piro,Oscar E., Castellano,Eduardo E.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000200012
• topic: 1,2,5-oxadiazole N-oxide; D-labeled furoxan; mass fragmentation; EI/MS

This paper reported on the study of fragmentation pattern in mass spectrometry of 1,2,5-oxadiazole N-oxide derivatives involving deuterium-labeled analogues to identify some critical fragmentations. A neutral CH2O loss from 3-hydroxymethyl-N2-oxide-4-phenyl-1,2,5-oxadiazole was confirmed with the corresponding mono-deuterated analogue. An OH loss, involving the oxygen of N-oxide, via beta-H and delta-H rearrangement, was clearly revealed from 3-(4-methylpiperazine-1-ylmethyl)-N2 -oxide-4-phenyl-1,2,5-oxadiazole using the adequate tetra-deuterated analogue. N-oxide isomer and deoxygenated analogues were also used to confirm the participation of the oxide moiety in the fragmentation process.