C. Berti, L. Greci, M. Poloni
1980
Citations
0
Influential Citations
7
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
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.