6533b7d5fe1ef96bd12650ff

RESEARCH PRODUCT

Electron Ionization Induced Fragmentation of some 3-Aroylamino-5-Methyl-1,2,4- Oxadiazoles and 3-Acetylamino-5-Aryl-1,2,4-Oxadiazoles

Vincenzo FrennaDomenico SpinelliLeopoldo CerauloCarla BogaV. Di StefanoDavid BongiornoSerena IndelicatoGiuseppe AvelloneL. Zuppiroli

subject

Mass spectrometryStereochemistryArylOrganic ChemistryMass spectrometryPhotochemistrychemistry.chemical_compoundEI induced rearrangementchemistryFragmentation (mass spectrometry)Boulton-Katritzky Reactions (BKR)Fragmentation mechanism3-Acylamino-124-oxadiazolesElectron ionization

description

: Background and objectives. 1,2,4-Oxadiazoles show a high reactivity and represent starting compounds for the synthesis of several other heterocycles. Some their derivatives can give the so called Boulton-Katritzky Reactions (BKR) which opens the way to the synthesis of several azoles. For this reason we have registered the mass spectra of several 3-aroylamino-5-methyl-1,2,4-oxadiazoles and 3-acetylamino-5-aryl-1,2,4-oxadiazoles. Methods and results. Thus, studying the mass spectra of the isomeric couple 3-benzoylamino-5-methyl-1,2,4-oxadiazole (1A) and 3-acetylamino-5-phenyl-1,2,4-oxadiazoles (1B) we have observed that MIKE and CID MIKE spectra of their molecular ions and of the [M – CH2CO]+. evidence that several fragmentation processes arise from common structure(s). Conclusions. These findings lead to suggest that the BKR could occur also under electron ionization. In order to evidence possible substituent effects the EI-MS spectra of a large series of 3-aroylamino-5-methyl-1,2,4-oxadiazoles (2A-19A) and of the corresponding 3-acetylamino-5-aryl-1,2,4-oxadiazoles (2B-19B) have been examined.

10.2174/1385272821666170601125344http://hdl.handle.net/11585/615837