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Beta-hydroxytryptamines. I. Chemical Synthesis of 3-(2-Amino- 1-hydroxyethyl)indole and 5-Hydroxy-3-(2-amino-l-Hydroxy-ethyl)indole

V. Plavšić ; Institute »Ruder Boskovic«, 41000 Zagreb, Croatia, Yugoslavia
S. Kveder ; Institute »Ruder Boskovic«, 41000 Zagreb, Croatia, Yugoslavia
S. Iskrić ; Institute »Ruder Boskovic«, 41000 Zagreb, Croatia, Yugoslavia

Sažetak

From indole and 5-benzyloxyindole, respectively, the corresponding
chloromethyl 3-indolyl ketones were prepared applying
Guignard reaction with chloroacetyl chloride or Vilsmeier reaction
with N,N-diethylchloroacetamide. By i. r. and n. m. r. spectroscopy
it was proved that identical compounds were obtained in both
reactions.
After the substitution of the halide with dibenzylamino group
and the reduction of the carbonyl group to hydroxyl with lithium
alumi.num hydride, benzyl groups were removed by catalytic
hydrogenation.
3-(2-Amino-1-hydroxyethy l)indole (beta-hydroxytryptamine)
and 5-hydroxy-3-(2-amino-1-hydroxyethyl)indole (beta-hydroxyserotonin)
were isolated in the form of crystalline creatinine
sulphates. Solubility and satisfying stability in aqueous solutions
make these salts suitable for biochemical and pharmaco'logical
investigations.

Ključne riječi

Hrčak ID:

196818

URI

https://hrcak.srce.hr/196818

Datum izdavanja:

21.12.1974.

Posjeta: 491 *