Synthesis of 3-acyl-5-hydroxyindoles and 3-acyl-5-hydroxybenzofurans. Influence of solvent on the course of the Nenitzescu reaction

TI Mukhanova, LM Alekseeva, EF Kuleshova…

Index: Mukhanova, T. I.; Alekseeva, L. M.; Kuleshova, E. F.; Sheinker, Yu. N.; Granik, V. G. Pharmaceutical Chemistry Journal, 1993 , vol. 27, # 2 p. 136 - 142 Khimiko-Farmatsevticheskii Zhurnal, 1993 , vol. 27, # 2 p. 60 - 65

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Abstract

136 0091-150X/93/2702-0136512.50 9 1993 Plenum Publishin~ Corporation reaction. Thus the reaction of benzoquinone (I) with l-acetyl-2-amino-l-propene (IIa) leads to a mixture of 2- methyl-3-acetyl-5-hydroxyindole (III, R= H)(IIIa) and-benzofuran (IV)[5], but the use of the N- methyl (IIb) and N-ethyl derivatives of enaminoketone IIa gave only the benzofuran IV [3]. Conversely, treatment of quinone I with the corresponding N-aryl analogs (IIc and IId) ...