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Reactions of 3-Hydrazino-1,2,4-triazino[5,6-b]indole with alfa, beta-unsaturated ketones, esters and nitriles

Youssef A. S. A.

Bulletin of the Polish Academy of Sciences. Chemistry

2001

Vol. 49, No. 1

9-16

3-Hydrazino-l,2,4-triazino[5,6-b]indole (1) reacted with l-aryl-3-phenylprop- 2-yn-l-ones (Ila-c) to give 3-1'-(5'-aryl-3'-phenyl)pyrazolyl] 1,2,4-triazino[5,6-b]indoles (Illa-c). o;-(p-Chlorobenzoyl) acephenone-N-3(l,2,4-triazino[5,6-b]indole) hydrazone (IV) was isolated in case of (lib) only. On the other hand, methyl p-chlorophenyl prop-2-ynoate (lid) gave 3-[1'-(3'-p-chlorophenyl-5'-hydroxy) pyrazolyl] l,2,4-triazino[5,6-b]indo-le (Hid). (I) reacted with diethyl but-2-yndioate (VI) to give 3-[1'-(3'-carboethoxy-4'-hydro-5'-oxo) pyrazolyl] l,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) l,2,4-triazino[5,6-b] indoles, respectively.