Synthesis of fused 4,5-disubstituted indole ring systems by intramolecular friedel-crafts acylation of 4-substituted indoles.
4-Substituted indoles containing a variety of electrophiles and N-substituents undergo Friedel-Crafts acylation to give exclusively the products of cyclization at the 5-position of indole. These indanones and tetralones have been scarcely prepared and are subunits in natural products and analogues of potential biological significance.
Fillion
Eric
E
Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada. efillion@uwaterloo.ca
Dumas
Aaron M
AM
D000215:Acylation; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D007211:Indoles