58810-39-2

Usage

Structure

Bicyclic, with a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring

Substituents

A benzoyloxy group attached to position 1 of the indole ring and a phenyl group attached to position 2

Uses

Organic synthesis and pharmaceutical research, key intermediate in the production of various pharmaceuticals and agrochemicals

Importance

Valuable building block for the synthesis of complex organic compounds due to its structural properties and reactivity.

Upstream product

• 1613-37-2 Quinoline N-oxide 
• 1859-39-8 2-phenyl-N-hydroxyindole 
• 98-88-4 benzoyl chloride 
• 100-42-5 styrene 
• 577-19-5 2-nitrophenyl bromide 
• 4264-29-3 (E)-2-nitrostilbene 

Downstream Products

• 64968-18-9 1-benzoyloxy-2-phenyl-3-(2-quinolyl)indole 
• 57152-69-9 2-phenyl-1H-indol-3-yl benzoate 
• 64968-19-0 1-hydroxy-2-phenyl-3-(2-quinolyl)indole 

Relevant academic research and scientific papers

Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles

tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.

STUDIES ON TERTIARY AMINE OXIDES. LXXII. SOME NUCLEOPHILIC REACTIONS OF 1-HYDROXY-2-PHENYLINDOLE

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