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^*

^*Corresponding author for this work

Department of Chemistry

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

7 Citations (Scopus)

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.).

Original language	English
Pages (from-to)	3142-3153
Number of pages	12
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	18
DOIs	https://doi.org/10.1002/adsc.201700546
Publication status	Published - 2017 Sept 18

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201700546

Cite this

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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}",

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language = "English",

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AU - Villuri, Bharath Kumar

AU - Konala, Ashok

AU - Kavala, Veerababurao

AU - Kotipalli, Trimurtulu

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1540780: Experimental Crystal Structure Determination

CCDC 1540781: Experimental Crystal Structure Determination

CCDC 1540779: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1540780: Experimental Crystal Structure Determination

CCDC 1540781: Experimental Crystal Structure Determination

CCDC 1540779: Experimental Crystal Structure Determination

Cite this