Synthesis of new (pyrazol-1-yl)(7-nitro-1h-indol-2-yl)ketone derivatives

Abstract

International audienceThe condensation of 7-nitroindole-2-carbohydrazide derivatives with acetylacetone lead to (pyrazol-1-yl)(7-nitroindol-2-yl)ketones

Ethyl 2-[(Z)-2-(2-nitrophenyl)hydrazinylidene]propanoate

“…Phenylhydrazones represent the principal starting material in the synthesis of indole derivatives. Some works have reported the synthesis of indole derivatives from the mixture of the two tautomers of phenylhydrazone without separation (Parmerter et al, 1958;Murakami et al, 1999;Narayana et al, 2005;El Kihel et al, 2013). Among these, Murakami et al (1999) reported the separation of the mixture of indole normal and indole abnormal.…”

“…However, the synthesis of phenylhydrazone by the condensation of phenylhydrazine with carbonyl compounds or by condensation of o-nitroaniline diazonium with ethyl -methylacetoacetate in basic medium (Japp-Klingemann reaction) lead to two tautomeric products (Murakami et al, 1993;Wagaw et al, 1999;Lipinska et al, 1999). Based on our indole synthesis program (El Kihel et al, 2013, 2007El Ouar et al, 1995), we report in this work the isolation of the majority product of the mixture of the two tautomers.…”

Crystal structure of (Z)-ethyl 3-[2-(5-methyl-7-nitro-1H-indole-2-carbonyl)hydrazinylidene]butanoate

“…For biochemical properties of indoles, see: Kuethe et al (2005); Smith et al (1998). For medicinal activity, see: El Kihel et al (2007Kihel et al ( , 2013; Penning et al (1997); Dumas et al (2000). For starting materials, see: El Ouar et al (1995 Symmetry codes: (i) Àx þ 1; Ày; Àz þ 2; (ii) x; y þ 1; z þ 1; (iii) Àx þ 1; Ày; Àz þ 1.…”

“…In previous papers (El Kihel et al, 2007;2013;El Ouar et al, 1995), we have reported some reactions of 7-aminoindoles and the condensation of the 7-nitroindole-2-carbohydrazide with acetylacetone. Herein, we report the Table 2.…”