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

48 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",

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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.

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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

Cite this