Novel trends in the chemistry of acridines. New fluorescent bioreagents and synthons on the basis of 9-isothiocyanatoacridines

9-Isothiocyanatoacridines containing a reactive NCS group, together with a biologically active acridine skeleton, were used for the synthesis of new acridine heterocycles. Their reactivity with aliphatic and aromatic amines as well as 15 amino acids was quantified by kinetic measurements. Sodium D-alkyl-N-(9-acridinyl)iminothiocarbonates obtained by addition of sodium alkoxides to the title compounds gave three types of products with organic halogen reagents. The reaction of above iminothiocarbonates with alkyl halides led to the fluorescent S-alkyl derivatives, whereas bromoacetyl bromide and alkyl bromoacetates afforded the 3-(9acridinyl)-1, 3-thiazolidine-2,4-diones and a new heterocycle, spiro[dihydroacridine-9(IOH), 4'-thiazoline], respectively.Department of Organic Chemistry, P. J. Safarik University, 04167 Kosice, Slovak Republic. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1376–1379, October, 1995. Original article submitted July 1, 1995