Construction of a Polycyclic Conjugated System Containing a Dibenzazepine Moiety by Cationic Gold(I)-Catalyzed Cycloisomerization

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Abstract

A new π-conjugated system of nitrogen-containing polycyclic compounds was constructed by cationic AuI-catalyzed cycloisomerization. Intramolecular reaction of 9-(2-alkynylphenyl)-9H-carbazole derivatives gave a variety of penta- and hexacyclic compounds possessing a dibenzazepine skeleton. The rigid carbazole structure was responsible for efficient 7-endo-dig cycloisomerization.

Original languageEnglish
Pages (from-to)5234-5237
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number31
DOIs
Publication statusPublished - 2016 Nov 1

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carbazoles
Gold
Polycyclic Compounds
gold
Rigid structures
musculoskeletal system
Nitrogen
Derivatives
nitrogen
dibenzazepine
carbazole

Keywords

  • Conjugation
  • Cycloisomerization
  • Gold
  • Nitrogen heterocycles
  • Polycycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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abstract = "A new π-conjugated system of nitrogen-containing polycyclic compounds was constructed by cationic AuI-catalyzed cycloisomerization. Intramolecular reaction of 9-(2-alkynylphenyl)-9H-carbazole derivatives gave a variety of penta- and hexacyclic compounds possessing a dibenzazepine skeleton. The rigid carbazole structure was responsible for efficient 7-endo-dig cycloisomerization.",
keywords = "Conjugation, Cycloisomerization, Gold, Nitrogen heterocycles, Polycycles",
author = "Mamoru Ito and Ryosuke Kawasaki and Kanyiva, {Stephen Kyalo} and Takanori Shibata",
year = "2016",
month = "11",
day = "1",
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language = "English",
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T1 - Construction of a Polycyclic Conjugated System Containing a Dibenzazepine Moiety by Cationic Gold(I)-Catalyzed Cycloisomerization

AU - Ito, Mamoru

AU - Kawasaki, Ryosuke

AU - Kanyiva, Stephen Kyalo

AU - Shibata, Takanori

PY - 2016/11/1

Y1 - 2016/11/1

N2 - A new π-conjugated system of nitrogen-containing polycyclic compounds was constructed by cationic AuI-catalyzed cycloisomerization. Intramolecular reaction of 9-(2-alkynylphenyl)-9H-carbazole derivatives gave a variety of penta- and hexacyclic compounds possessing a dibenzazepine skeleton. The rigid carbazole structure was responsible for efficient 7-endo-dig cycloisomerization.

AB - A new π-conjugated system of nitrogen-containing polycyclic compounds was constructed by cationic AuI-catalyzed cycloisomerization. Intramolecular reaction of 9-(2-alkynylphenyl)-9H-carbazole derivatives gave a variety of penta- and hexacyclic compounds possessing a dibenzazepine skeleton. The rigid carbazole structure was responsible for efficient 7-endo-dig cycloisomerization.

KW - Conjugation

KW - Cycloisomerization

KW - Gold

KW - Nitrogen heterocycles

KW - Polycycles

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U2 - 10.1002/ejoc.201601147

DO - 10.1002/ejoc.201601147

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VL - 2016

SP - 5234

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 31

ER -