95256-27-2Relevant academic research and scientific papers
Studies on Tertiary Amine Oxides. LXXIX. Reactions of 2-Ethoxycarbonyl-1-hydroxyindole in the Presence of Acylating Agents
Nagayoshi, Tsuyoshi,Saeki, Seitaro,Hamana, Masatomo
, p. 3678 - 3682 (2007/10/02)
The Vilsmeier-Haack reaction of 2-ethoxycarbonyl-1-hydroxyindole (2) did not give 3-formylindoles but gave 3-chloro-2-ethoxycarbonylindole (3).The electrophilic reaction of 2 with quinoline 1-oxide (4) in the presence of benzoyl chloride or tosyl chloride also failed, 1-benzoyloxy-2-ethoxycarbonylindole (6) or 3 being formed, respectively.The reaction of 2 with tosyl chloride, benzoyl chloride or acetic anhydride gave the corresponding 3-acyloxy-2-ethoxycarbonylindoles (7, 8 and 11) in unsatisfactory yields.Treatment of 2 with tosyl chloride and 1-morpholinocyclohexene in pyridine-dimethylformamide afforded 2-ethoxycarbonyl-3-(2-oxocyclohexyl)indole (13) after hydrolysis of the reaction mixture.Keywords - enehydroxylamine; nucleophilic reaction; 3-chloro-2-ethoxycarbonylindole; 3-acyloxy-2-ethoxycarbonylindole; 2-ethoxycarbonyl-3-(2-oxocyclohexyl)indole; quinoline 1-oxide; 1-morpholinocyclohexene.
