Investigation of the Synthesis of Benzofuroindolines from N-Hydroxyindoles: An O-Arylation/[3,3]-Sigmatropic Rearrangement Sequence

Terry Tomakinian; Cyrille Kouklovsky; Guillaume Vincent

doi:10.1055/s-0034-1380346

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(09): 1269-1275
DOI: 10.1055/s-0034-1380346

letter

Investigation of the Synthesis of Benzofuroindolines from N-Hydroxyindoles: An O-Arylation/[3,3]-Sigmatropic Rearrangement Sequence

Terry Tomakinian

Univ Paris Sud and CNRS, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR8182, Equipe Méthodologie, Synthèse & Molécules Thérapeutiques (MS&MT), Bat. 410, 91405 Orsay, France eMail: guillaume.vincent@u-psud.fr

,

Cyrille Kouklovsky

Univ Paris Sud and CNRS, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR8182, Equipe Méthodologie, Synthèse & Molécules Thérapeutiques (MS&MT), Bat. 410, 91405 Orsay, France eMail: guillaume.vincent@u-psud.fr

,

Guillaume Vincent*

Univ Paris Sud and CNRS, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR8182, Equipe Méthodologie, Synthèse & Molécules Thérapeutiques (MS&MT), Bat. 410, 91405 Orsay, France eMail: guillaume.vincent@u-psud.fr

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Abstract

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Dedicated to Dr. Patrick Y. S. Lam

Abstract

We report the demonstration that sensitive N-hydroxyindoles can be O-arylated under transition-metal-free conditions with biaryliodonium salts. The subsequent spontaneous [3,3]-sigmatropic rearrangement delivers benzofuroindolines derived from tryptamine. We also describe the practical synthesis of N-hydroxyindoles by oxidation of indolines with m-CPBA.

Key words

N-hydroxyindoles - diazonamide A - azonazine - benzofuroindoline - [3,3]-sigmatropic rearrangement

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Referenzen

References and Notes

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