1. Swern oxidation of tryptamine derivatives
- Author
-
Frances Irvine, Patrick D. Bailey, Keith M. Morgan, David P. J. Pearson, Kenneth T. Veal, and Philip J. Cochrane
- Subjects
Indole test ,Tryptamine ,Reaction conditions ,chemistry.chemical_compound ,chemistry ,Nucleophile ,Organic Chemistry ,Drug Discovery ,Swern oxidation ,Substrate (chemistry) ,Organic chemistry ,Biochemistry - Abstract
The Swern oxidation of various indolic substrates is described, and a range of products resulting from overalloxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to α,β-unsaturated systems at the 2-position, to introduce a nucleophile at the 2-position, and to introduce a CH3-S-CH2 group at the indole 4-position via an unprecedented rearrangement of a Swern intermediate.
- Published
- 1999