73822-13-6

Upstream product

• 73822-10-3 (2S,3R)-3-Methyl-2-phenyl-2,3-dihydro-indole-1,3-diol 
• 1137-96-8 N-(benzylidene)aniline N-oxide 
• 57309-13-4 3-hydroxy-3-methyl-2-phenyl-3H-indole-1-oxide 

Downstream Products

• 57309-13-4 3-hydroxy-3-methyl-2-phenyl-3H-indole-1-oxide 
• 73822-19-2 C₁₅H₁₂NO 

Relevant academic research and scientific papers

Rh(III)-Catalyzed C-H Cyclization of Arylnitrones with Diazo Compounds: Access to 3-Carboxylate Substituted N-Hydroxyindoles

Recently, N-hydroxyindole derivatives have received much interest because of their unique structural motif and various biological activities. In this study, we report the first example of a Rh(III)-catalyzed reaction of arylnitrones with α-diazoketoesters or α-diazodiketones to produce N-hydroxyindole derivatives. Intriguingly, we could build the N-hydroxyindole scaffold by blocking the cleavage of the N-O bond selectively, while eliminating the acyl group of α-diazoketoesters or α-diazodiketones preferentially.

Stereospecific Reduction of 3-Hydroxy-3H-indoles and of their Corresponding N-Oxides with NaBH4 and LiAlH4. Synthesis of True 1-Hydroxy-2,3-disubstituted Indoles. Crystal and Molecular Structure of 3-Hydroxy-2,3-diphenylindoline

3-Hydroxy-3H-indoles (1) and their corresponding N-oxides (5) undergo stereospecific reduction at the double C=N bond giving the indoline derivatives (2) and (6) respectively, which, in acidic medium, lose water to give the 2,3-disubstituted indoles (3) and (7) whose physical and spectroscopic data are not in agreement with those reported previously.The structure of 3-hydroxy-2,3-diphenylindoline, one of the reduction products, was determined by X-ray diffraction, and it was shown that hydrogen adds at C-2 cis to the hydroxy-group on C-3. 3,3-Disubstituted-3H-indoles with two organic radicals on C-3 give a mixture of stereoisomers.