Croatica Chemica Acta, Vol. 33 No. 2, 1961.
Original scientific paper
The Synthesis of 3,5-Disubstituted Indoles by Cyclization under Mild Conditions
D . Keglević
; Tracer Laboratory, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
N. Stojanac
; Tracer Laboratory, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
D. Desaty
; Tracer Laboratory, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
Abstract
3-Benzyloxy-6-fo~mylaminotoluene (III) could not be converted
by Madelung cyclization into the corresponding indole derivative.
It was found, that 4-aminobutanal diethyl acetal and p-benzyloxyphenylhydrazine hydrochloride cyclize into 5-benzyloxytryptamine hydrochloride (V) in 250/o acetic acid at 800 in 68° /o yield. Under these mild conditions a lso other 3,5-substituted indoles were obtained: 3-methyl-5-benzyloxyindole (VI), 3-ethyl-5-benzyloxyindole (VII), 5-methoxytryptamine picrate (VIII) and N'-acetyl-5-
methoxytryptamine (Melatonin, IX).
Keywords
Hrčak ID:
208444
URI
Publication date:
10.10.1961.
Visits: 628 *