Tetrahedron Letters p. 4717 - 4720 (1992)
Update date:2022-08-04
Topics:
Chung, John Y. L.
Reamer, Robert A.
Reider, Paul J.
The intramolecular Friedel-Crafts acylation of 2-(3-indolylthio)propionic acid 1 has been found to undergo an unprecedented rearrangement to provide a novel tricyclic indole having the sulfur substituted on C-4 rather than on the expected C-3.A mechanism for its formation is proposed.This rearrangement also proceeded with good optical retention when a chiral substrate was used.Key Words: Friedel-Crafts acylation; rearrangement; tricyclic indoles; 4-thio-indoles; thiopyrano<4,3,2-c,d>indoles.
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