144174-41-4

Downstream Products

• 144174-45-8 4-[(R)-5-(4-Chloro-benzyl)-8-hydroxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indol-4-yl]-3,3-dimethyl-butyronitrile 
• 144174-44-7 4-[(R)-5-(4-Chloro-benzyl)-3-hydroxy-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indol-4-yl]-3,3-dimethyl-butyronitrile 

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.