MASS-SPECTRAL STUDIES OF 6-NORMAL-PROPYL-2-THIOURACIL, ITS OXYGEN, SELENIUM AND FLUORINATED CONGENERS

The electron ionization mass spectra of the clinically used antithyroid agent 6-n-propyl-2-thiouracil (la), its minor metabolite, 6-n-propyluracil (lb) and their synthetic selenium and fluorinated analogs (1c and d) have been examined. The fragmentation pattern of these thiouracil and selenouracil studied bear strong similarities with those previously derived from a study of uracil analogs. Thus, the first step in the fragmentation is a retro Diel-Alder decomposition with the loss of HCNX (X=0, S or Se) and the production of an ion radical which undergoes further fragmentation pathways which are discussed. 6-n- Propy1-2-selenouracil (1c) did show more complicated spectra due to the six natural isotopic abundance exhibited by the selenium atom. While the fluorinated analogs (Id) did substantiate the fact that the fragmentation pattern of these derivatives proceed through fragmentation between C2 and N3 bond since this produces the more resonance stabilized ion. © 1990, Taylor & Francis Group, LLC. All rights reserved.