Dearomative Oxidative Rearrangement of [3]Cyclo-1,8-carbazolylene

Masamichi Yasui; Hiroyoshi Ohtsu; Masaki Kawano; Kengo Hanaya; Takeshi Sugai; Shuhei Higashibayashi

doi:10.1246/cl.180637

Dearomative Oxidative Rearrangement of [3]Cyclo-1,8-carbazolylene

Masamichi Yasui, Hiroyoshi Ohtsu, Masaki Kawano, Kengo Hanaya, Takeshi Sugai, Shuhei Higashibayashi

School of Pharmaceutical Sciences

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

Abstract

[3]Cyclo-1,8-carbazolylene was found to undergo oxidative rearrangement by oxidation with 2,3-dichloro-5,6-dicyano-pbenzoquinone, giving a 9a-substituted carbazol-1-one derivative. This is the first example of a dearomative oxidative rearrangement of a carbazole or aniline derivative. The geometrical and electronic structures were elucidated by X-ray analysis, UV-vis absorption spectroscopy, and DFT calculations.

Original language	English
Pages (from-to)	1357-1359
Number of pages	3
Journal	Chemistry Letters
Volume	47
Issue number	11
DOIs	https://doi.org/10.1246/cl.180637
Publication status	Published - 2018

Keywords

Carbazole
Oxidation
Rearrangement

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.180637

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title = "Dearomative Oxidative Rearrangement of [3]Cyclo-1,8-carbazolylene",

abstract = "[3]Cyclo-1,8-carbazolylene was found to undergo oxidative rearrangement by oxidation with 2,3-dichloro-5,6-dicyano-pbenzoquinone, giving a 9a-substituted carbazol-1-one derivative. This is the first example of a dearomative oxidative rearrangement of a carbazole or aniline derivative. The geometrical and electronic structures were elucidated by X-ray analysis, UV-vis absorption spectroscopy, and DFT calculations.",

keywords = "Carbazole, Oxidation, Rearrangement",

author = "Masamichi Yasui and Hiroyoshi Ohtsu and Masaki Kawano and Kengo Hanaya and Takeshi Sugai and Shuhei Higashibayashi",

note = "Funding Information: This work was supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Numbers 17K19131 (S. H.), 26102002 (S. H.), and JST ACT-C Grant Number JPMJCR12YZ (S. H.). The X-ray diffraction study of 10 with synchrotron radiation was performed at the Pohang Accelerator Laboratory (Beamline 2D) supported by POSTECH.",

year = "2018",

doi = "10.1246/cl.180637",

language = "English",

volume = "47",

pages = "1357--1359",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "11",

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TY - JOUR

T1 - Dearomative Oxidative Rearrangement of [3]Cyclo-1,8-carbazolylene

AU - Yasui, Masamichi

AU - Ohtsu, Hiroyoshi

AU - Kawano, Masaki

AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Higashibayashi, Shuhei

N1 - Funding Information: This work was supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Numbers 17K19131 (S. H.), 26102002 (S. H.), and JST ACT-C Grant Number JPMJCR12YZ (S. H.). The X-ray diffraction study of 10 with synchrotron radiation was performed at the Pohang Accelerator Laboratory (Beamline 2D) supported by POSTECH.

PY - 2018

Y1 - 2018

N2 - [3]Cyclo-1,8-carbazolylene was found to undergo oxidative rearrangement by oxidation with 2,3-dichloro-5,6-dicyano-pbenzoquinone, giving a 9a-substituted carbazol-1-one derivative. This is the first example of a dearomative oxidative rearrangement of a carbazole or aniline derivative. The geometrical and electronic structures were elucidated by X-ray analysis, UV-vis absorption spectroscopy, and DFT calculations.

AB - [3]Cyclo-1,8-carbazolylene was found to undergo oxidative rearrangement by oxidation with 2,3-dichloro-5,6-dicyano-pbenzoquinone, giving a 9a-substituted carbazol-1-one derivative. This is the first example of a dearomative oxidative rearrangement of a carbazole or aniline derivative. The geometrical and electronic structures were elucidated by X-ray analysis, UV-vis absorption spectroscopy, and DFT calculations.

KW - Carbazole

KW - Oxidation

KW - Rearrangement

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JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

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