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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

11 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	17505-17510
頁數	6
期刊	Journal of Organic Chemistry
卷	88
發行號	24
DOIs	https://doi.org/10.1021/acs.joc.3c01857
出版狀態	已發佈 - 2023 12月 15

ASJC Scopus subject areas

有機化學

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10.1021/acs.joc.3c01857

其它文件與鏈接

CCDC 2284824: Experimental Crystal Structure Determination
Suresh, S. (Contributor), Chien, H.-S. (Contributor), Chen, C.-H. (Contributor), Tsai, H.-Y. (Contributor), Chung, D.-R. (Contributor), Kavala, V. (Contributor) & Yao, C.-F. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2gpk0r, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2gpk0r&sid=DataCite
資料集: Dataset
CCDC 2284823: Experimental Crystal Structure Determination
Suresh, S. (Contributor), Chien, H.-S. (Contributor), Chen, C.-H. (Contributor), Tsai, H.-Y. (Contributor), Chung, D.-R. (Contributor), Kavala, V. (Contributor) & Yao, C.-F. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2gpjzp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2gpjzp&sid=DataCite
資料集: Dataset
CCDC 2284822: Experimental Crystal Structure Determination
Suresh, S. (Contributor), Chien, H.-S. (Contributor), Chen, C.-H. (Contributor), Tsai, H.-Y. (Contributor), Chung, D.-R. (Contributor), Kavala, V. (Contributor) & Yao, C.-F. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2gpjyn, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2gpjyn&sid=DataCite
資料集: Dataset

引用此

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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",

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journal = "Journal of Organic Chemistry",

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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.

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UR - https://www.scopus.com/pages/publications/85179607610#tab=citedBy

U2 - 10.1021/acs.joc.3c01857

DO - 10.1021/acs.joc.3c01857

M3 - Article

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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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 2284824: Experimental Crystal Structure Determination

CCDC 2284823: Experimental Crystal Structure Determination

CCDC 2284822: Experimental Crystal Structure Determination

引用此