Synthesis of benzo[: A] carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile

Chun Wei Kuo; Ashok Konala; Lyu Lin; Ting Ta Chiang; Chia Yu Huang; Tang Hao Yang; Veerababurao Kavala; Ching Fa Yao

doi:10.1039/c6cc03124b

Synthesis of benzo[: A] carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile

Chun Wei Kuo
, Ashok Konala
, Lyu Lin
, Ting Ta Chiang
, Chia Yu Huang
, Tang Hao Yang
, Veerababurao Kavala
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

51 Citations (Scopus)

Abstract

The dual character of benzoquinone is exploited for the synthesis of benzo[a]carbazole derivatives starting from 3-ethylindole derivatives. A diene is generated in situ from the 3-ethylindole derivative with the help of benzoquinone, where it acts as an oxidizing agent. Later it serves as a dienophile and participates in a Diels-Alder reaction with the diene to afford benzo[a]carbazole derivatives.

Original language	English
Pages (from-to)	7870-7873
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	50
DOIs	https://doi.org/10.1039/c6cc03124b
Publication status	Published - 2016

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c6cc03124b

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title = "Synthesis of benzo[: A] carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile",

abstract = "The dual character of benzoquinone is exploited for the synthesis of benzo[a]carbazole derivatives starting from 3-ethylindole derivatives. A diene is generated in situ from the 3-ethylindole derivative with the help of benzoquinone, where it acts as an oxidizing agent. Later it serves as a dienophile and participates in a Diels-Alder reaction with the diene to afford benzo[a]carbazole derivatives.",

author = "Kuo, \{Chun Wei\} and Ashok Konala and Lyu Lin and Chiang, \{Ting Ta\} and Huang, \{Chia Yu\} and Yang, \{Tang Hao\} and Veerababurao Kavala and Yao, \{Ching Fa\}",

note = "Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6cc03124b",

language = "English",

volume = "52",

pages = "7870--7873",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "50",

}

TY - JOUR

T1 - Synthesis of benzo[

T2 - A] carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile

AU - Kuo, Chun Wei

AU - Konala, Ashok

AU - Lin, Lyu

AU - Chiang, Ting Ta

AU - Huang, Chia Yu

AU - Yang, Tang Hao

AU - Kavala, Veerababurao

AU - Yao, Ching Fa

PY - 2016

Y1 - 2016

N2 - The dual character of benzoquinone is exploited for the synthesis of benzo[a]carbazole derivatives starting from 3-ethylindole derivatives. A diene is generated in situ from the 3-ethylindole derivative with the help of benzoquinone, where it acts as an oxidizing agent. Later it serves as a dienophile and participates in a Diels-Alder reaction with the diene to afford benzo[a]carbazole derivatives.

AB - The dual character of benzoquinone is exploited for the synthesis of benzo[a]carbazole derivatives starting from 3-ethylindole derivatives. A diene is generated in situ from the 3-ethylindole derivative with the help of benzoquinone, where it acts as an oxidizing agent. Later it serves as a dienophile and participates in a Diels-Alder reaction with the diene to afford benzo[a]carbazole derivatives.

UR - https://www.scopus.com/pages/publications/84975092153

UR - https://www.scopus.com/pages/publications/84975092153#tab=citedBy

U2 - 10.1039/c6cc03124b

DO - 10.1039/c6cc03124b

M3 - Article

AN - SCOPUS:84975092153

SN - 1359-7345

VL - 52

SP - 7870

EP - 7873

JO - Chemical Communications

JF - Chemical Communications

IS - 50

ER -

Synthesis of benzo[: A] carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile

Abstract

ASJC Scopus subject areas

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CCDC 1457405: Experimental Crystal Structure Determination

CCDC 1457406: Experimental Crystal Structure Determination

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Synthesis of benzo[: A] carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1457405: Experimental Crystal Structure Determination

CCDC 1457406: Experimental Crystal Structure Determination

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