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Synthesis of 6,7,8,9-tetrahydropyrido[2,3-b]indolizine and 3,4-dihydro-2H-pyrido[2′,3′:4,5]pyrrolo[2,1-b][1,3]oxazine derivatives as new melatonin receptor ligands

✍ Scribed by Hervé Van de Poël; Gérald Guillaumet; Marie-Claude Viaud-Massuard

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 216 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)02359-0

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✦ Synopsis

The synthesis of new tricyclic azaindolic analogs of the hormone melatonin is described. Treatment of 1-(4-bromobutyl)pyrrolo[3,2-b]pyridine derivative with tributyltin hydride and AIBN results in radical cyclisation to give the 6,7,8,9-tetrahydropyrido[2,3-b]indolizine ring system. A new synthetic approach of pyridopyrrolo[2,1-b][1,3]oxazine moiety is shown to be accomplished readily from 1-(3-bromopropyl)-2-oxopyrrolopyridine derivative with sodium hydride in N,N-dimethylformamide.

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