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Report | Regular issue | Vol 12, No. 6, 1979, pp.811-814
Published online, 1st January, 1970
DOI: 10.3987/R-1979-06-0811
The “One Pot” Photochemical Synthesis of 2-Methyl-3-carboethoxy-5-phenylindole

René Beugelmans,* Hélène Ginsburg, Marie-Thérèse Le Goff, Alexandra Lecas, Jacques Pusset, and Georges Roussi

*Institut des Chimie des Substances Naturelles, C.N.R.S., 1 avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France

Abstract

The title compound 6 is obtained by UV irradiation of 4-nitro-biphenyl in the presence of diethyl malonate anion. The very complex course of the process, involving reactions (a, b, c, d, e) is discussed and a sequence of intermediates 2, 3, 4, 5 is proposed.
a) Intermolecular nitro group reduction with ethyl malonate incorporation (hν) ; b) dehydration ; c) decarboxylation ; d) cyclization ; e) deoxygenation.