Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles

Sundaram Suresh; Hung Sheng Chien; Chao Hua Chen; Hao Yu Tsai; Dai Ru Chung; Veerababurao Kavala; Ching Fa Yao

doi:10.1021/acs.joc.3c01857

Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles

Sundaram Suresh, Hung Sheng Chien, Chao Hua Chen, Hao Yu Tsai, Dai Ru Chung, Veerababurao Kavala, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

4 Citations (Scopus)

Abstract

The [4 + 2] annulation of β-formyl ketones with an indole has been developed for the regioselective synthesis of diphenyl-substituted carbazoles in the presence of a catalytic amount of iodine. The 1,4-dicarbonyl compound containing a phenyl group at the α-position of an aldehyde group reacts more readily with indoles to form carbazole derivatives. Using this method, a variety of carbazole derivatives can be readily accessed under mild reaction conditions.

Original language	English
Pages (from-to)	17505-17510
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	88
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.3c01857
Publication status	Published - 2023 Dec 15

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.3c01857

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title = "Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles",

abstract = "The [4 + 2] annulation of β-formyl ketones with an indole has been developed for the regioselective synthesis of diphenyl-substituted carbazoles in the presence of a catalytic amount of iodine. The 1,4-dicarbonyl compound containing a phenyl group at the α-position of an aldehyde group reacts more readily with indoles to form carbazole derivatives. Using this method, a variety of carbazole derivatives can be readily accessed under mild reaction conditions.",

author = "Sundaram Suresh and Chien, {Hung Sheng} and Chen, {Chao Hua} and Tsai, {Hao Yu} and Chung, {Dai Ru} and Veerababurao Kavala and Yao, {Ching Fa}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = dec,

day = "15",

doi = "10.1021/acs.joc.3c01857",

language = "English",

volume = "88",

pages = "17505--17510",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "24",

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T1 - Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles

AU - Suresh, Sundaram

AU - Chien, Hung Sheng

AU - Chen, Chao Hua

AU - Tsai, Hao Yu

AU - Chung, Dai Ru

AU - Kavala, Veerababurao

AU - Yao, Ching Fa

PY - 2023/12/15

Y1 - 2023/12/15

N2 - The [4 + 2] annulation of β-formyl ketones with an indole has been developed for the regioselective synthesis of diphenyl-substituted carbazoles in the presence of a catalytic amount of iodine. The 1,4-dicarbonyl compound containing a phenyl group at the α-position of an aldehyde group reacts more readily with indoles to form carbazole derivatives. Using this method, a variety of carbazole derivatives can be readily accessed under mild reaction conditions.

AB - The [4 + 2] annulation of β-formyl ketones with an indole has been developed for the regioselective synthesis of diphenyl-substituted carbazoles in the presence of a catalytic amount of iodine. The 1,4-dicarbonyl compound containing a phenyl group at the α-position of an aldehyde group reacts more readily with indoles to form carbazole derivatives. Using this method, a variety of carbazole derivatives can be readily accessed under mild reaction conditions.

UR - http://www.scopus.com/inward/record.url?scp=85179607610&partnerID=8YFLogxK

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U2 - 10.1021/acs.joc.3c01857

DO - 10.1021/acs.joc.3c01857

M3 - Article

AN - SCOPUS:85179607610

SN - 0022-3263

VL - 88

SP - 17505

EP - 17510

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles

Abstract

ASJC Scopus subject areas

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CCDC 2284823: Experimental Crystal Structure Determination

CCDC 2284824: Experimental Crystal Structure Determination

CCDC 2284822: Experimental Crystal Structure Determination

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Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles

Abstract

ASJC Scopus subject areas

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Fingerprint

Datasets

CCDC 2284823: Experimental Crystal Structure Determination

CCDC 2284824: Experimental Crystal Structure Determination

CCDC 2284822: Experimental Crystal Structure Determination

Cite this