The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry.
Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.
Somei
M
M
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan. somei@dbs.p.kanazawa-u.ac.jp
Yamada
F
F
Kurauchi
T
T
Nagahama
Y
Y
Hasegawa
M
M
Yamada
K
K
Teranishi
S
S
Sato
H
H
Kaneko
C
C
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D012701:Serotonin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis; D014363:Tryptamines / Q000737:chemistry*
D000470:Alkaloids; D007211:Indoles; D014363:Tryptamines; D012701:Serotonin; C030820:tryptamine