- Lithiation of 1-alkoxyindole derivatives
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Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.
- Nakagawa, Kyoko,Kobayashi, Tetsuya,Kawasaki, Toshiya,Somei, Masanori
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p. 968 - 997
(2019/04/26)
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- 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
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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,Yamada,Kurauchi,Nagahama,Hasegawa,Yamada,Teranishi,Sato,Kaneko
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- SIMPLE SYNTHESES OF LESPEDAMINE AND 5-BROMO-N,N-DIMETHYLTRYPTAMINE BASED ON 1-HYDROXYINDOLE CHEMISTRY
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Various types of 1-hydroxyindoles were prepared for the first time.Through methylation or acid catalyzed nucleophilic bromination of N,N-dimethyl-1-hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.
- Somei, Masanori,Kobayashi, Kensuke,Tanii, Keiko,Mochizuki, Toshihiko,Kawada, Yumiko,Fukui, Yoshikazu
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p. 119 - 122
(2007/10/02)
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- A SHORT STEP SYNTHESIS OF LESPEDAMINE
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A convenient synthetic method for 1-hydroxy-, 1-methoxy-, and 1-acetoxy-2-oxindole was disclosed starting from methyl 2-nitrophenylacetate.A five-step synthesis of lespedamine was achieved utilizing this method.
- Somei, Masanori,Sato, Haruhiko,Kaneko, Chikara
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p. 1797 - 1799
(2007/10/02)
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