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 le...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2001, Vol.49 (1), p.87-96
Hauptverfasser:	SOMEI, Masanori, YAMADA, Fumio, KURAUCHI, Takashi, NAGAHAMA, Yoshiyuki, HASEGAWA, Masakazu, YAMADA, Koji, TERANISHI, Sakiko, SATO, Haruhiko, KANEKO, Chikara
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indoles - chemistry Molecular Structure Organic chemistry Preparations and properties Serotonin - analogs & derivatives Serotonin - chemical synthesis Serotonin - chemistry Spectrum Analysis Tryptamines - chemistry
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Zusammenfassung:	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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.49.87