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8‐ exo ‐ dig ‐Selective Cycloisomerization for the Synthesis of Dibenzo[ b , e ][1,4]diazocines Using Cationic Au I Catalysts
Author(s) -
Ito Mamoru,
Inoue Daisuke,
Takaki Asahi,
Kanyiva Kyalo Stephen,
Shibata Takanori
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801037
Subject(s) - cycloisomerization , chemistry , cationic polymerization , dig , catalysis , propargyl , stereochemistry , ligand (biochemistry) , intramolecular force , medicinal chemistry , organic chemistry , receptor , biochemistry , computer security , computer science
The cationic Au I ‐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 Au I 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.