Glyoxal monohydrate reacts with N-alkylanilines to give substituted 3-anilinoindoles and anilinoacetanilides in a ratio which, in the absence of catalysts, depends on the amount of water present. Acid catalysts favour formation of indoles. The reaction mechanism is discussed. A single crystal X-ray diffraction study of 5-chloro-3-(4-chloro-N-methylanilino)-1-methylindole (XVIII) is reported: the crystals are monoclinic, with unit-cell dimensions of a = 13.96, b = 13.34, c = 8.96 Å, and β = 114°33′ space-group P21/c.

Substituted 3-anilinoindoles and anilinoacetanilides from the reaction of glyoxal with N-alkylanilines: crystal structure of 5-chloro-3-(4-chloro-N-methylanilino)-1-methylindole / P. Ferruti, A. Ferè, A. Bettelli, M. Zocchi, G. Tieghi, A. Albinati. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - (1972), pp. 2001-2003.

Substituted 3-anilinoindoles and anilinoacetanilides from the reaction of glyoxal with N-alkylanilines: crystal structure of 5-chloro-3-(4-chloro-N-methylanilino)-1-methylindole

A. Albinati
1972

Abstract

Glyoxal monohydrate reacts with N-alkylanilines to give substituted 3-anilinoindoles and anilinoacetanilides in a ratio which, in the absence of catalysts, depends on the amount of water present. Acid catalysts favour formation of indoles. The reaction mechanism is discussed. A single crystal X-ray diffraction study of 5-chloro-3-(4-chloro-N-methylanilino)-1-methylindole (XVIII) is reported: the crystals are monoclinic, with unit-cell dimensions of a = 13.96, b = 13.34, c = 8.96 Å, and β = 114°33′ space-group P21/c.
Settore CHIM/03 - Chimica Generale e Inorganica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/190964
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