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

Mamoru Ito; Ryosuke Kawasaki; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1002/ejoc.201601147

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

Mamoru Ito, Ryosuke Kawasaki, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

A new π-conjugated system of nitrogen-containing polycyclic compounds was constructed by cationic Au^I-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 language	English
Pages (from-to)	5234-5237
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	31
DOIs	https://doi.org/10.1002/ejoc.201601147
Publication status	Published - 2016 Nov

Keywords

Conjugation
Cycloisomerization
Gold
Nitrogen heterocycles
Polycycles

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201601147

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

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, {Kyalo Stephen} and Takanori Shibata",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

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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, Kyalo Stephen

AU - Shibata, Takanori

PY - 2016/11

Y1 - 2016/11

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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EP - 5237

JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

SN - 1434-193X

IS - 31

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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