Identification of photoproducts of hexahydroquinoline derivatives by GC-EI-MS and HPLC-ESI-MS

Photoproducts of hexahydroquinoline derivatives have been analyzed with gas chromatography electro ionization-mass spectrometry (GC-EI-MS) and high performance chromatography electrospray ionization-mass spectrometry (HPLC-ESI-MS). The study was performed on four HHQ derivatives: 2,6,6-trimethyl-3-carbomethoxy-5-oxo-4-(R-phenyl)-1,4,5,6,7,8 hexahydroquinoline; R=2'-Me, 3'-Me, 2'-MeO, and 3'-MeO. The photochemical degradation of each of the HHQ derivatives led to the appearance of one product. The photoproducts were identified as the corresponding tetrahydroquinoline analogues, which were formed by dehydrogenation of dihydropyridine moiety. In GC-mass spectra, the most frequent way of fragmentation was elimination of CH3* or CH3O* radical of the ester group. In the photoproducts substituted at 2'-position of the phenyl ring, elimination of isobutene (C4H8) was observed. In the photoproducts with 3'-position substituents, elimination of COOCH3* radical was noted.