Synthesis of N‐Fused Tricyclic Indoles by a Tandem [1,2] Stevens‐Type Rearrangement/1,2‐Alkyl Migration of Metal‐Containing Ammonium Ylides | Zendy

Takaya Jun | Zendy; Udagawa Shuji | Zendy; Kusama Hiroyuki | Zendy; Iwasawa Nobuharu | Zendy

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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).

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