77740-35-3Relevant academic research and scientific papers
Reactions of Ethyl 3-Ethoxymethylene-2,4-dioxovalerate and Ethyl Ethoxymethyleneoxaloacetate with Indole Analogs
Kurihara, Takushi,Tani, Tsutomu,Imai, Hiromi,Nasu, Keiko
, p. 2972 - 2979 (2007/10/02)
The reactions of ethyl 3-ethoxymethylene-2,4-dioxovalerate (1a) and ethyl ethoxymethyleneoxaloacetate (1b) with indole analogs (2, 14, 17-19) are described.Treatment of 1a, b with 2 in ethanol followed by refluxing in acetic anhydride afforded 3,4,10-trisubstituted pyrimidoindoles (4a, b).Hydrogenation or nucleophilic addition of 4a, b was found to occur on the pyrimidine ring in a 1,4-fashion.Compounds 1a, b were also reacted with 14 in ethanol under ice cooling to give the 3,4-disubstituted 9H-pyrimidoindoles (15a, b) directly.Indole (17) or 2-methylindole (18) reacted with 1a (or 1b) to give a mixture of 3-indolylmethylene derivatives (20a, b and 21a, b) and tris-(3-indolyl)-methanes (23 and 24).
