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Synlett 2015; 26(09): 1269-1275
DOI: 10.1055/s-0034-1380346
DOI: 10.1055/s-0034-1380346
letter
Investigation of the Synthesis of Benzofuroindolines from N-Hydroxyindoles: An O-Arylation/[3,3]-Sigmatropic Rearrangement Sequence
Further Information
Publication History
Received: 22 December 2014
Accepted after revision: 16 February 2015
Publication Date:
01 April 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201509/lookinside/thumbnails/st-2014-d1051-l_10-1055_s-0034-1380346-1.jpg)
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 rearrangementSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380346.
- Supporting Information
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References and Notes
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For biological interest, see:
For total and formal synthesis, see:
For reviews on the synthesis of benzofuroindolines, see:
For selected examples, see: