Synthesis of 7-Alkoxy/Hydroxy-α-methyltryptamines

A simple method for the preparation of 7-alkoxy/hydroxy-α-methyl-DL-tryptamines is reported. The key steps of the synthesis are the Japp-Klingemann coupling of 2-piperidone-3-carboxylic acid 3 with diazonium salts 4, the Fischer-type cyclization of hydrazones 5 to β-carboline derivatives 6 and their...

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Bibliographic Details
Published inSynthetic communications Vol. 34; no. 10; pp. 1791 - 1799
Main Authors Dubash, Nauzer P., Mangu, Naveen K., Satyam, Apparao
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 31.12.2004
Taylor & Francis
Subjects
7-Benzyloxy-α-methyltryptamine
7-Hydroxy-α-methyltryptamine
7-Methoxy-α-methyltryptamine
Chemistry
Chemistry, Organic
Japp-Klingemann coupling
Physical Sciences
Reductive amination
Science & Technology
7-benzyioxy-alpha-methyltryptamine
7-hydroxy-alpha-methyltryptamine
Japp-Klingemann coupling
7-methoxy-alpha-methyltryptamine
reductive amination
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Summary:A simple method for the preparation of 7-alkoxy/hydroxy-α-methyl-DL-tryptamines is reported. The key steps of the synthesis are the Japp-Klingemann coupling of 2-piperidone-3-carboxylic acid 3 with diazonium salts 4, the Fischer-type cyclization of hydrazones 5 to β-carboline derivatives 6 and their hydrolysis to title compounds 8.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-120034160