Synthesis and Spectroscopic Study of Some New 1,2,4-Triazino[5,6-b]indole Derivatives

Abstract

The Scheme of this work included the synthesis and characterization of new two series of 1,2,4-triazino[5,6-b] indole and 8-bromo-1,2,4-triazino[5,6-b] indole derivatives according to the starting material used. Both, derivatives of 3-thione-1,2,4-triazino[5,6-b] indole and 8-bromo-3-thione-1,2,4-triazino[5,6-b] indole (3a & 3b) were prepared by using Isatin and 5-bromo isatin as a starting material, the new schiff`s bases (5a & 5b) were synthesized by the reaction of hydrazino indole derivatives (4a & 4b) with aromatic aldehydes. Tetracyclic derivatives (7a & 7b) were prepared by the reaction of hydrazino derivatives (4a & 4b) with carbon disulfide in the presence of pyridine. Also 3-(N-phenyl thiocarbamoyl hydrazino)-1,2,4-triazino-[5,6-b] indole, and 8-bromo-3-(N phenyl thiocarbamoyl hydrazino)-1,2,4-triazino-[5,6-b] indole (6a & 6b) were prepared by the reaction of the compound (4a & 4b) with phenyl thio isocyanate in the presence of DMF. Finally, new Mannich bases (9a & 9b) were prepared by the reaction of the new acetylenic indole derivatives (8a & 8b) with paraformaldehyde and secondary amine in the presence of coprous chloride as catalyst. These compounds were identified by their melting points and spectral data (IR & UV), and elemental analysis (C,H,N) and thin layer chromatography (TLC) were used.