The similar reaction of diquinodithiin 1 with hydrochlorides of 1-naphthylamine, 2-naphthylamine, and 6-aminoquinoline gave pentacyclic 7H-quinonaphthothiazine 4, 14H-quinonaphthothiazine 5, and 7H-diquinothiazine 6. The reaction of isomeric diquinodithiin 7 with acetamide and p-fluoroaniline hydrochloride gave linearly condensed pentacyclic 6H-diquinothiazines 9a and 6-(p-fluorophenyl)diquinothiazine 9b (Scheme 2). Analogous reaction of another isomeric diquinodithiin 10 with p-fluoroaniline hydrochloride led to angularly condensed diquinothiazine 12c. Better yields of the fluoroaniline products 9b and 12c were achieved when x,x’-dichloro-3,3′-diquinolinyl sulfides 8 and 11 (x = 2 and

4) were used. Sulfide 11 reacted also with ammonia or methylamine in hot phenol to give diquinothiazines

12a, b. Scheme 1 Reactans: a C6H5NH2·HCl CX-6258 concentration (p-ClC6H4NH2·HCl, p-CH3OC6H4NH2·HCl), 200–205 °C, 4 h; b p-CH3OC6H4NH2, MEDG, reflux, 3 h; c 1-naphthylamine·HCl, 200–205 °C, 4 h; d 2-naphthylamine·HCl, 200–205 °C, 4 h; e 6-aminoquinoline·HCl, 200–205 °C, 4 h Scheme 2 Reactans: a CH3CONH2, K2CO3, 180 °C, 0.5 h; b pF-C6H4NH2·HCl), 200–205 °C, 3 h; c p-FC6H4NH2, MEDG, reflux, 3 h; d NH3 (CH3NH2), phenol, 180 °C, 1 h The described syntheses were monitored by TLC analysis. All chromatograms of new compounds showed characteristic for azaphenothiazines (Jeleń et al., 2011) color changing during irradiation with UV light from blue to yellow (4, Adenosine triphosphate 9b), from yellow to green (5, 6), from orange to yellow (12c), and from yellow to orange (7c). Structure It is well Nutlin-3a mw known that the synthesis of phenothiazines can proceed via the Smiles rearrangement of the S–N type of the appropriate sulfide (Pluta et al., 2009). The identification of the product structures was based on the spectroscopic 1H NMR and MS analysis. In the case of the reactions of sulfides 7 and 11, the products 9 and 12 possessed the C2v symmetry (the left part was a mirror image of the right one) what excluded the stage of rearrangement. The reactions of diquinodithiin 1 and disulfide 2 with anilines proceeded similarly

without the stage of rearrangement to give tetracyclic quinobenzothiazines 3a–c (Jeleń and Pluta, 2009). The reaction with 1-naphthylamine gave pentacyclic quinonaphthothiazine 4. On the contrary, the reactions with 2-naphthylamine and 6-aminoquinoline were more complex as there were two possibilities of the thiazine ring formation. The 1H NMR analysis of the reaction products pointed at compounds 5 and 6 excluding compounds 13 and 14, as evidenced from coupling Wortmannin constants; the H-5 and H-6 protons in compounds 5 and 6 showed a coupling constant J ortho, whereas analogous protons in compounds 13 and 14 (H-7/H-12 and H-5/H-14, respectively) would have shown a coupling constant J para, which is very small (i.e., J 1,4 = 0.6-0.