A Copper-Catalyzed Cascade Approach for the Synthesis of Dibenzo[b,f]1,8-naphthyridine Derivatives

Bharath Kumar Villuri; Ashok Konala; Veerababurao Kavala; Trimurtulu Kotipalli; Chun Wei Kuo; Ching Fa Yao

doi:10.1002/adsc.201700546

A Copper-Catalyzed Cascade Approach for the Synthesis of Dibenzo[b,f]1,8-naphthyridine Derivatives

Bharath Kumar Villuri, Ashok Konala, Veerababurao Kavala, Trimurtulu Kotipalli, Chun Wei Kuo, 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

5 引文斯高帕斯（Scopus）

摘要

The synthesis of some dibenzo[b,f]-[1,8]naphthyridine derivatives in a cascade manner is reported. The reaction includes a Knovenagel condensation, the insertion of a nitrile and an alkyne into an N–H bond and an oxidation/oxidative C–C bond cleavage sequence in the presence of copper iodide. The key 1,8-naphthyridine core was constructed in a cascade manner during the course of the reaction itself which allows diverse dibenzo[b,f]-[1,8]naphthyridine derivatives to be readily prepared. (Figure presented.).

原文	英語
頁（從 - 到）	3142-3153
頁數	12
期刊	Advanced Synthesis and Catalysis
卷	359
發行號	18
DOIs	https://doi.org/10.1002/adsc.201700546
出版狀態	已發佈 - 2017 九月 18

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催化
有機化學

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@article{930842aafae34739b186c1ef7c5bd6a4,

title = "A Copper-Catalyzed Cascade Approach for the Synthesis of Dibenzo[b,f]1,8-naphthyridine Derivatives",

abstract = "The synthesis of some dibenzo[b,f]-[1,8]naphthyridine derivatives in a cascade manner is reported. The reaction includes a Knovenagel condensation, the insertion of a nitrile and an alkyne into an N–H bond and an oxidation/oxidative C–C bond cleavage sequence in the presence of copper iodide. The key 1,8-naphthyridine core was constructed in a cascade manner during the course of the reaction itself which allows diverse dibenzo[b,f]-[1,8]naphthyridine derivatives to be readily prepared. (Figure presented.).",

keywords = "1,8-naphthyridines, aurora kinase inhibitor, cascade reaction, hydroamination, tandem insertion",

author = "Villuri, {Bharath Kumar} and Ashok Konala and Veerababurao Kavala and Trimurtulu Kotipalli and Kuo, {Chun Wei} and Yao, {Ching Fa}",

note = "Funding Information: Financial support by the Ministry of Science and Technology of the Republic of China (MOST 103-2113-M-003-008-MY3), National Taiwan Normal University (103-07-C) and Instrumentation Centre at National Taiwan Normal University is gratefully acknowledged. The authors are grateful to Ms. Hsiu-Ni Huan, Ms. Chiu-Hui He and Ting-Shen Kuo for providing HR-MS, NMR spectra, and crystallographic data, respectively. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = sep,

day = "18",

doi = "10.1002/adsc.201700546",

language = "English",

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T1 - A Copper-Catalyzed Cascade Approach for the Synthesis of Dibenzo[b,f]1,8-naphthyridine Derivatives

AU - Villuri, Bharath Kumar

AU - Konala, Ashok

AU - Kavala, Veerababurao

AU - Kotipalli, Trimurtulu

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

N1 - Funding Information: Financial support by the Ministry of Science and Technology of the Republic of China (MOST 103-2113-M-003-008-MY3), National Taiwan Normal University (103-07-C) and Instrumentation Centre at National Taiwan Normal University is gratefully acknowledged. The authors are grateful to Ms. Hsiu-Ni Huan, Ms. Chiu-Hui He and Ting-Shen Kuo for providing HR-MS, NMR spectra, and crystallographic data, respectively. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/9/18

Y1 - 2017/9/18

N2 - The synthesis of some dibenzo[b,f]-[1,8]naphthyridine derivatives in a cascade manner is reported. The reaction includes a Knovenagel condensation, the insertion of a nitrile and an alkyne into an N–H bond and an oxidation/oxidative C–C bond cleavage sequence in the presence of copper iodide. The key 1,8-naphthyridine core was constructed in a cascade manner during the course of the reaction itself which allows diverse dibenzo[b,f]-[1,8]naphthyridine derivatives to be readily prepared. (Figure presented.).

AB - The synthesis of some dibenzo[b,f]-[1,8]naphthyridine derivatives in a cascade manner is reported. The reaction includes a Knovenagel condensation, the insertion of a nitrile and an alkyne into an N–H bond and an oxidation/oxidative C–C bond cleavage sequence in the presence of copper iodide. The key 1,8-naphthyridine core was constructed in a cascade manner during the course of the reaction itself which allows diverse dibenzo[b,f]-[1,8]naphthyridine derivatives to be readily prepared. (Figure presented.).

KW - 1,8-naphthyridines

KW - aurora kinase inhibitor

KW - cascade reaction

KW - hydroamination

KW - tandem insertion

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A Copper-Catalyzed Cascade Approach for the Synthesis of Dibenzo[b,f]1,8-naphthyridine Derivatives

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