64968-23-6Relevant articles and documents
STUDIES ON TERTIARY AMINE OXIDES. LXXII. SOME NUCLEOPHILIC REACTIONS OF 1-HYDROXY-2-PHENYLINDOLE
Nagayoshi, Tsuyoshi,Saeki, Seitaro,Hamana, Masatomo
, p. 1920 - 1926 (2007/10/02)
1-Hydroxy-2-phenylindole (1) reacts with tosyl chloride and p-nitrobenzenesulfonyl chloride in DMF-pyridine to give the corresponding 2-phenyl-3-sulfonyloxyindole (2 and 4).Benzoyl chloride is less reactive, and 1-benzoyloxy-2-phenylindole (5) or 3-benzoyloxy-2-phenylindole (6) is formed, depending upon the reaction conditions. 3-Acetoxy-2-phenylindole (7) is also obtained by refluxing 1 with acetic anhydride or with acetyl chloride in DMF-pyridine.Treatment of 1 with tosyl chloride and then with 1-morpholinocyclohexene (9), ethyl acetoacetate (17) and ethyl cyanoacetate (20) in DMF-pyridine at room temperature affords 3-(2-oxocyclohexyl)-2-phenylindole (10), ethyl α-(2-phenyl-3-indolyl)acetoacetate (18) and ethyl α-(2-phenyl-3-indolyl)cyanoacetate (21) in 23.2, 41 and 61percent yields, respectively.Keywords: enehydroxylamine system; 1-acyloxy-2-phenylindole; 3-acyloxy-2-phenylindole; 1-morpholinocyclohexene; 3-(2-oxocyclohexyl)-2-phenylindole; ethyl α-(2-phenyl-3-indolyl)acetoacetate; ethyl α-(2-phenyl-3-indolyl)cyanoacetate