Reactions of 3-hydrazino-1,2,4-triazino[5,6-b]indole with α,β-unsaturated ketones, esters and nitriles

3-Hydrazino-1,2,4-triazino[5,6-b]indole (I) reacted with 1-aryl-3-phenylprop-2-yn-1-ones (IIa-c) to give 3-[1'-(5'-aryl-3'-phenyl)pyrazolyl] 1,2,4-triazino[5,6-b]indoles (IIIa-c). omega-(p-Chlorobenzoyl) acephenone-N-3(1,2,4-triazino[5,6-b]indole) hydrazone (IV) was isolated in case of (IIb) only. On the other hand, methyl p-chlorophenyl prop-2-ynoate (IId) gave 3-[1'-(3'-p-chlorophenyl-5'-hydroxy) pyrazolyl] 1,2,4-triazino[5,6-b]indole (IIId). (I) reacted with diethyl but-2-yndioate (Vf) to give 3-[1'-(3'-carboethoxy-4'-hydro-5'-oxo) pyrazolyl] 1,2,4-triazino[5,6-b]indole (VII) and diethyl oxaloacetate- N-3-(1,2,4-triazino[5,6-b] indole) hydrazone (VIII). Similar treatment of (I) with 2-cyano-(IXa) or 2-cyano-3-methyl- (IXb) cinnamonitriles afforded 3-[2'-(4'-phenylmethylene- 3',5'-dioxo-4'-hydro) pyrazolyl] -(Xa) or 3-[2'-(4'-methyl phenylmethylene-3',5'-dioxo-4'-hydro) pyrazolyl]- (Xb) 1,2,4-triazino[5,6-b] indoles, respectively.