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Synthesen von Mannich‐Basen von Hydroxy‐indolen. 3. Mitteilung über synthetische Indol‐Verbindungen [1]
Author(s) -
Troxler F.,
Bormann G.,
Seemann F.
Publication year - 1968
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19680510603
Subject(s) - chemistry , indole test , reactivity (psychology) , mannich reaction , stereochemistry , electrophile , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Abstract The reactivity of hydroxy‐indoles under the conditions of the Mannich‐reaction has been studied. The electrophilic side‐chain enters in each case in a position ortho to the phenolic group. 4‐Hydroxy‐indole is substituted in the 5‐, 5‐hydroxy‐indole in the 4‐, 6‐hydroxy‐indole in the 7‐, and 7‐hydroxy‐indole probably in the 6‐position. The structures of the Mannich bases from 4‐, 5‐ and 6‐hydroxy‐indole have been confirmed by comparison of the hydroxy‐methyl‐indoles obtained by reductive desamination with hydroxy‐methyl‐indoles prepared by unambiguous total synthesis.