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Mass spectrometry of 2‐substituted‐4‐arylthiazoles: II–identification of microsomal nitroreduction product by mass spectrometry
Author(s) -
Mattammal Michael B.,
Zenser Terry V.,
Davis Bernard B.
Publication year - 1982
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200090904
Subject(s) - chemistry , thiazole , mass spectrometry , fragmentation (computing) , electron ionization , molecule , ion , cleavage (geology) , stereochemistry , ionization , organic chemistry , chromatography , geotechnical engineering , fracture (geology) , computer science , engineering , operating system
Electron impact fragmentation of 2‐methyl‐4‐(4‐nitropenyl)‐thiazole and 2‐amino‐4‐(4‐nitrophenyl)‐thiazoles were studied. Prominent fragment ions result from: (1) elimination of an NO 2 radical and of a neutral NO molecule; (2) 1,2 cleavage of the thiazole ring in both compounds to give a phenoxythiirene ion; and (3) subsequent cleavage of this phenoxythiirene ion to give the common ions [C 7 H 5 ] and [C 5 H 3 ]. An anaerobic microsomal nitroreduction product of 2‐methyl‐4‐(4‐nitrophenyl) thiazole was isolated and its structure was determined by electron impact, chemical ionization and high resolution mass spectrometry to be 2‐methyl‐4‐(4‐aminophenyl)‐thiazole.