23829-47-2Relevant academic research and scientific papers
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
Berti, Corrado,Greci, Lucedio,Poloni, Marino,Andreetti, Giovanni Dario,Bocelli, Gabriele,Sgarabotto, Paolo
, p. 339 - 346 (2007/10/02)
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.
