✦ LIBER ✦

The solid-phase Nenitzescu indole synthesis

✍ Scribed by Daniel M Ketcha; Lawrence J Wilson *; David E Portlock

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 157 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00697-3

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✦ Synopsis

The solid-phase version of the Nenitzescu indole synthesis of 5-hydroxyindole-3-carboxamides is reported. This process involves initial acetoacetylation of ArgoPore 1 -Rink-NH 2 resin with diketene to aord a polymer-bound acetoacetamide. Formation of the corresponding enaminones via condensation with primary amines in the presence of trimethylorthoformate followed by addition of 1,4-benzoquinones leads to the desired indoles after TFA induced cleavage from the resin.

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