One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A.
The reaction of (2-aminobenzyl) triphenylphosphonium bromide with aromatic aldehydes or alpha,beta-unsaturated aldehydes under microwave-assisted conditions constitutes a new synthesis of 2-substituted indoles in high yields (81-97%) in a one-pot reaction. The adduct from indole-4-carboxaldehyde was an advanced intermediate in the synthesis of arcyriacyanin A.
Kraus
George A
GA
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA. gakraus@iastate.edu
Guo
Haitao
H
D001593:Benzyl Compounds / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008301:Maleimides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*
D001593:Benzyl Compounds; D007211:Indoles; D008301:Maleimides; D009943:Organophosphorus Compounds; C406440:arcyriacyanin A