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8‐exo‐dig‐Selective Cycloisomerization for the Synthesis of Dibenzo[b,e][1,4]diazocines Using Cationic AuI Catalysts

The cationic AuI‐catalyzed intramolecular reaction of N‐propargyl‐2‐anilinoanilines gave a diazocine skeleton via 8‐exo‐dig‐selective cycloisomerization by the suppression of 6‐endo‐dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-09, Vol.2018 (34), p.4740-4747
Main Authors: Ito, Mamoru, Inoue, Daisuke, Takaki, Asahi, Kanyiva, Kyalo Stephen, Shibata, Takanori
Format: Article
Language:eng ; jpn
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Summary:The cationic AuI‐catalyzed intramolecular reaction of N‐propargyl‐2‐anilinoanilines gave a diazocine skeleton via 8‐exo‐dig‐selective cycloisomerization by the suppression of 6‐endo‐dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation. The cationic AuI‐catalyzed intramolecular reaction of N‐propargyl‐2‐anilinoanilines gave a diazocine skeleton via 8‐exo‐dig‐selective cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex. Two nitrogen atoms in the tether of substrates were critical in this selective transformation.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201801037