144174-40-3

Upstream product

• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 144174-42-5 6-Bromo-3,3-dimethyl-5-oxo-hexanenitrile 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 62646-04-2 1-(4-chlorobenzyl)-1-(4-methoxyphenyl)hydrazine 
• 144174-43-6 (R)-2-(5-Cyano-4,4-dimethyl-2-oxo-pentylsulfanyl)-propionic acid 

Relevant academic research and scientific papers

Friedel-Crafts Cyclization of 2-(3-Indolylthio)propionic Acids. An Unusual Rearrangement Leading to 4-Sulfur-Substituted Tricyclic Indoles

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; thiopyranoindoles.