Premium
Synthesis of N‐Fused Tricyclic Indoles by a Tandem [1,2] Stevens‐Type Rearrangement/1,2‐Alkyl Migration of Metal‐Containing Ammonium Ylides
Author(s) -
Takaya Jun,
Udagawa Shuji,
Kusama Hiroyuki,
Iwasawa Nobuharu
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705517
Subject(s) - moiety , alkyl , alkyne , chemistry , amine gas treating , ammonium , tandem , indole test , medicinal chemistry , tricyclic , catalysis , stereochemistry , organic chemistry , materials science , composite material
An alkyne moiety is activated efficiently with a [W(CO) 6 ] or [ReBr(CO) 5 ] catalyst in the presence of an amine functionality in the title reaction of N ‐(2‐alkynylphenyl)amines. The resulting ammonium ylides undergo rearrangement to form a variety of N‐fused polycyclic indole derivatives (see scheme; n =1,2; R=alkyl, Ph).