A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.
The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or alpha,beta-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4-dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines.
Kraus
George A
GA
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA. gakraus@iastate.edu
Guo
Haitao
H
D000447:Aldehydes / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism; D052999:Quinazolinones
D000447:Aldehydes; D026121:Indole Alkaloids; D009943:Organophosphorus Compounds; D011799:Quinazolines; D012492:Salts; C545161:(2-aminobenzyl)triphenylphosphonium bromide; C028632:rutecarpine; D052999:Quinazolinones