Stereospecific reduction of 3-hydroxy-3H-indoles and of their corresponding N-oxides with NaBH4 and LiAIH4. Synthesis of true 1-hydroxy-2,3-disubstituted indoles. Crystal and molecular structure of 3-hydroxy-2,3-diphenylindoline
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 2,p. 339-346
- https://doi.org/10.1039/p29800000339
Abstract
3-Hydroxy-3H-indoles (1) and their corresponding N-oxides (5) undergo stereospecific reduction at the double CN 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.Keywords
This publication has 0 references indexed in Scilit: