Regiospecific synthesis, structure and electron ionization mass spectra of 1,3-thiazolidin-4-ones containing the acridine skeleton

The synthesis of regioisomeric 3-alkyl(aryl)-2-(acridin-9′-yl)imino-1,3-thiazolidin-4-ones (8b-i) and 2-alkyl(aryl)imino-3-(acridin-9′-yl)-1,3-thiazolidin-4-ones (11a-i) was performed by the reaction of 3-(acridin-9-yl)-1-alkyl(aryl)thioureas 5a-i with methyl bromoacetate and bromoacetyl bromide, respectively, via the corresponding isothiourea hydrobromides with excellent regioselectivity. The structure, NMR spectra and mass spectrometric behavior of the resulting compounds are discussed.