Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate
The 5-substituted tetrazole ring was reacted in the gas phase with an acyl ion generated as the secondary reactive chemical ionization plasma in the mass spectrometer. The product ions obtained, among others, were proposed as the rearranged 2,5-disubstituted-1,3,4-oxadiazole nucleus. Its structure w...
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2001
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paper:paper_10765174_v36_n9_p1069_Seldes2023-06-08T16:05:22Z Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate Seldes, Alicia Marta D'Accorso, Norma Beatriz Martins Alho, Miriam Amelia Gas-phase reaction Heterocycles Ion-molecule reaction Rearrangement Derivatives Ionization Mass spectrometry Spectrum analysis Gas-phase conversion Aromatic compounds 1,2,3,4 di o isopropylidene beta levo arabinopyranos 5 yl 2 phenyl 5 glycosyl 1,3,4 oxadiazole nitrogen oxadiazole derivative pyrone derivative tetrazole derivative unclassified drug acetylation article chemical structure controlled study dissociation gas ionization mass spectrometer plasma priority journal tandem mass spectrometry Acylation Butanes Mass Spectrometry Oxadiazoles Tetrazoles The 5-substituted tetrazole ring was reacted in the gas phase with an acyl ion generated as the secondary reactive chemical ionization plasma in the mass spectrometer. The product ions obtained, among others, were proposed as the rearranged 2,5-disubstituted-1,3,4-oxadiazole nucleus. Its structure was demonstrated by comparison of the product ion spectrum of the 2,5-disubstituted-1,3,4-oxadiazole derivative obtained by condensed-phase reaction and the product ion spectrum of the oxadiazole derivative generated in situ by reaction of the 5-substituted tetrazole derivative with the acyl plasma. It was proposed that the mechanism of this transformation involved the presence of an acylated tetrazole intermediary, which could not be isolated in the condensed phase, followed by the rearrangement, with nitrogen loss, to afford the oxadiazole derivative. Under our conditions we were able to isolate the intermediate ion in the first field free region and demonstrate its structure by collision induced dissociation-tandem mass spectrometry. © 2001 John Wiley & Sons, Ltd. Fil:Seldes, A.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:D'Accorso, N. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Martins Alho, M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2001 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10765174_v36_n9_p1069_Seldes http://hdl.handle.net/20.500.12110/paper_10765174_v36_n9_p1069_Seldes |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Gas-phase reaction Heterocycles Ion-molecule reaction Rearrangement Derivatives Ionization Mass spectrometry Spectrum analysis Gas-phase conversion Aromatic compounds 1,2,3,4 di o isopropylidene beta levo arabinopyranos 5 yl 2 phenyl 5 glycosyl 1,3,4 oxadiazole nitrogen oxadiazole derivative pyrone derivative tetrazole derivative unclassified drug acetylation article chemical structure controlled study dissociation gas ionization mass spectrometer plasma priority journal tandem mass spectrometry Acylation Butanes Mass Spectrometry Oxadiazoles Tetrazoles |
| spellingShingle |
Gas-phase reaction Heterocycles Ion-molecule reaction Rearrangement Derivatives Ionization Mass spectrometry Spectrum analysis Gas-phase conversion Aromatic compounds 1,2,3,4 di o isopropylidene beta levo arabinopyranos 5 yl 2 phenyl 5 glycosyl 1,3,4 oxadiazole nitrogen oxadiazole derivative pyrone derivative tetrazole derivative unclassified drug acetylation article chemical structure controlled study dissociation gas ionization mass spectrometer plasma priority journal tandem mass spectrometry Acylation Butanes Mass Spectrometry Oxadiazoles Tetrazoles Seldes, Alicia Marta D'Accorso, Norma Beatriz Martins Alho, Miriam Amelia Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate |
| topic_facet |
Gas-phase reaction Heterocycles Ion-molecule reaction Rearrangement Derivatives Ionization Mass spectrometry Spectrum analysis Gas-phase conversion Aromatic compounds 1,2,3,4 di o isopropylidene beta levo arabinopyranos 5 yl 2 phenyl 5 glycosyl 1,3,4 oxadiazole nitrogen oxadiazole derivative pyrone derivative tetrazole derivative unclassified drug acetylation article chemical structure controlled study dissociation gas ionization mass spectrometer plasma priority journal tandem mass spectrometry Acylation Butanes Mass Spectrometry Oxadiazoles Tetrazoles |
| description |
The 5-substituted tetrazole ring was reacted in the gas phase with an acyl ion generated as the secondary reactive chemical ionization plasma in the mass spectrometer. The product ions obtained, among others, were proposed as the rearranged 2,5-disubstituted-1,3,4-oxadiazole nucleus. Its structure was demonstrated by comparison of the product ion spectrum of the 2,5-disubstituted-1,3,4-oxadiazole derivative obtained by condensed-phase reaction and the product ion spectrum of the oxadiazole derivative generated in situ by reaction of the 5-substituted tetrazole derivative with the acyl plasma. It was proposed that the mechanism of this transformation involved the presence of an acylated tetrazole intermediary, which could not be isolated in the condensed phase, followed by the rearrangement, with nitrogen loss, to afford the oxadiazole derivative. Under our conditions we were able to isolate the intermediate ion in the first field free region and demonstrate its structure by collision induced dissociation-tandem mass spectrometry. © 2001 John Wiley & Sons, Ltd. |
| author |
Seldes, Alicia Marta D'Accorso, Norma Beatriz Martins Alho, Miriam Amelia |
| author_facet |
Seldes, Alicia Marta D'Accorso, Norma Beatriz Martins Alho, Miriam Amelia |
| author_sort |
Seldes, Alicia Marta |
| title |
Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate |
| title_short |
Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate |
| title_full |
Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate |
| title_fullStr |
Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate |
| title_full_unstemmed |
Gas-phase conversion of tetrazoles to oxadiazoles: Isolation and characterization of the N-acylated intermediate |
| title_sort |
gas-phase conversion of tetrazoles to oxadiazoles: isolation and characterization of the n-acylated intermediate |
| publishDate |
2001 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10765174_v36_n9_p1069_Seldes http://hdl.handle.net/20.500.12110/paper_10765174_v36_n9_p1069_Seldes |
| work_keys_str_mv |
AT seldesaliciamarta gasphaseconversionoftetrazolestooxadiazolesisolationandcharacterizationofthenacylatedintermediate AT daccorsonormabeatriz gasphaseconversionoftetrazolestooxadiazolesisolationandcharacterizationofthenacylatedintermediate AT martinsalhomiriamamelia gasphaseconversionoftetrazolestooxadiazolesisolationandcharacterizationofthenacylatedintermediate |
| _version_ |
1768546759950204928 |