Synthesis of nitrogen-containing fused-polycyclic compounds from tyramine derivatives using phenol dearomatization and cascade cyclization

We developed a novel method of synthesizing nitrogen-containing fused-polycyclic compounds using tyramine derivatives as substrates. The method is based on the dearomatization of phenols via an intramolecular ipso-Friedel-Crafts allenylation and sequential bond-forming-cleavage reactions initiated b...

Full description

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 50; no. 84; pp. 12775 - 12778
Main Authors Yokosaka, Takuya, Nemoto, Tetsuhiro, Nakayama, Hiroki, Shiga, Naoki, Hamada, Yasumasa
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.10.2014
Subjects
Cascades
Catalysis
Chemistry
Chemistry, Multidisciplinary
Construction
Cyclization
Derivatives
Indoles
Lewis Acids - chemistry
Nitrogen - chemistry
Phenol
Phenol - chemistry
Physical Sciences
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Science & Technology
Substrates
Synthesis
Trifluoroacetic Acid - chemistry
Tyramine - chemistry
REARRANGEMENT
GOLD
ACTIVATION
ALKYLATION
CONSTRUCTION
INDOLES
SPIRO
Online AccessGet full text

Cover

More Information
Summary:We developed a novel method of synthesizing nitrogen-containing fused-polycyclic compounds using tyramine derivatives as substrates. The method is based on the dearomatization of phenols via an intramolecular ipso-Friedel-Crafts allenylation and sequential bond-forming-cleavage reactions initiated by the construction of an indole skeleton. Structurally diverse fused-heterocycles were produced in reaction sequences requiring only a few steps.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc04809a