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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

Sažetak

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).

Ključne riječi

Hrčak ID:

208444

URI

https://hrcak.srce.hr/208444

Datum izdavanja:

10.10.1961.

Posjeta: 622 *