Tetsuya Sekiba
Feb 1, 1973
Citations
0
Influential Citations
16
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
2,3-Dihydromaculosidine and 2,3-dihydropteleine were obtained from 2,4-dimethoxy- and 4-methoxy-aniline by condensation with diethyl β-benzyloxyethylmalonate, followed by methylation and subsequent cyclodebenzylation with polyphosphoric acid. The dehydrogenation of the dihydro compounds with 2,3-dichloro-5,6-dicyanobenzoquinone gave maculosidine (4,6,8-trimethoxyfuro[2,3-b]quinoline) and pteleine (4,6-dimethoxyfuro[2,3-b]quinoline) in relatively high yields. Similarly, evolitrine (4,7-dimethoxyfuro[2,3-b]quinoline) and γ-fagarine (4,8-dimethoxyfuro[2,3-b]quinoline) were also prepared.