10-CARBETHOXYMETHYL-3-PHENYL-1,2,4-TRIAZOLO[4',3'/2,3][1,2,4]TRIAZINO[5,6-B]INDOLE AND DERIVATIVES AT ITS 10-POSITION

Reaction of 3-phenyl-10H-1,2,4-triazolo[4',3':2,3][1,2,4]triazino[5,6-b]indole (4) with ethyl chloroacetate gave 10-carbethoxymethyl-3-phenyl-1,2,4-triazolo[4',3':2,3][1,2,4]triazino[5,6-b]indole (3). Condensation of 3 with hydrazine hydrate gave (3-phenyl-1,2,4-triazolo[4',3':2,3][1,2,4]triazino[5,6-b]indol-10-yl)acetylhydrazine (5). Reactions of 5 with a number of aromatic aldehydes, acetophenone, cyclohexanone and D-galactose gave the corresponding hydrazones 6-12. Condensation of 5 with acetyl-acetone gave the pyrazole 15. Cyclization of 5 with CS2 gave (3-phenyl-1,2,4-triazolo[4',3':2,3][1,2,4]triazino[5,6-b]indol-10-yl)(2-thiol-1,3,4-oxadiazol-5-yl)methane (16). Reaction of 16 with ethyl chloroacetate gave the carbethoxy alkylated derivative (3-phenyl-1,2,4-triazolo[4',3':2,3][1,2,4]triazino[5,6-b]indol-10-yl)[2-(thiocarbethoxymethyl)1,3,4-oxadiazol-5-yl]methane (17).