Iron-Facilitated Iodine-Mediated Electrophilic Annulation of N,N-Dimethyl-2-alkynylanilines with Disulfides or Diselenides

An efficient synthesis of N‐methyl‐3‐chalcogeno‐indoles has been developed via iodine‐mediated electrophilic annulation reactions of 2‐alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2‐alkynylanilines selectively underwent the electrophilic...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2011-10, Vol.353 (14-15), p.2739-2748
Main Authors: Du, Hui-Ai, Tang, Ri-Yuan, Deng, Chen-Liang, Liu, Yan, Li, Jin-Heng, Zhang, Xing-Guo
Format: Article
Language:English
Subjects:
2-alkynylanilines
3-selenenylindoles
3-sulfenylindoles
Catalysis
Chemistry
Derivatives
Disulfides
electrophilic annulation
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Iodine
Iron
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Synthesis
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Summary:An efficient synthesis of N‐methyl‐3‐chalcogeno‐indoles has been developed via iodine‐mediated electrophilic annulation reactions of 2‐alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2‐alkynylanilines selectively underwent the electrophilic annulation with numerous disulfides or diselenides leading to the corresponding 3‐sulfenylindoles and 3‐selenenylindoles in moderate to excellent yields. It is noteworthy that iron can promote the reaction.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201100349