The solid-phase Nenitzescu indole synthesis
2000; Elsevier BV; Volume: 41; Issue: 33 Linguagem: Inglês
10.1016/s0040-4039(00)00697-3
ISSN1873-3581
AutoresDaniel M. Ketcha, Lawrence J. Wilson, David E. Portlock,
Tópico(s)Chemical Synthesis and Reactions
ResumoThe solid-phase version of the Nenitzescu indole synthesis of 5-hydroxyindole-3-carboxamides is reported. This process involves initial acetoacetylation of ArgoPore®-Rink-NH2 resin with diketene to afford 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.
Referência(s)