Work

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.

Year: 2001

Type: article

Abstract: 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.

Source: Chemical and Pharmaceutical Bulletin

DOI: 10.1248/cpb.49.87

Authors: Masanori SOMEI, Fumio YAMADA, Takashi KURAUCHI, Yoshiyuki NAGAHAMA, Masakazu HASEGAWA, Koji YAMADA, Sakiko TERANISHI, Haruhiko SATO, Chikara KANEKO

Institution: Kanazawa University

Language: English

Topic: Synthesis of Indole Derivatives

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

OpenAlex ID: W2154587009

FWCI: 2.139

Cites: 37

Cited by: 40

Related to: 10