Swern oxidation of tryptamine derivatives

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.