Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines

Vijayalakshmi Bandi; Veerababurao Kavala; Che Hao Hsu; Ashok Konala; Bharath Kumar Villuri; Trimurtulu Kotipalli; Chun Wei Kuo; Ching Fa Yao

doi:10.1039/c7ra07128k

Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines

Vijayalakshmi Bandi, Veerababurao Kavala, Che Hao Hsu, Ashok Konala, Bharath Kumar Villuri, Trimurtulu Kotipalli, Chun Wei Kuo, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

2 Citations (Scopus)

Abstract

An approach for the synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives is reported starting from β-halo styrene and phenyl acetylene derivatives in the presence of PdCl₂ and CuI catalysts. Functional groups such as aldehyde, cyano and ester groups are well tolerated and afford the desired functionalized dienynes. Further, these 1,3-buta-diene-3-yne derivatives are utilized for the synthesis of novel trisubstituted pyridine derivatives.

Original language	English
Pages (from-to)	46704-46712
Number of pages	9
Journal	RSC Advances
Volume	7
Issue number	74
DOIs	https://doi.org/10.1039/c7ra07128k
Publication status	Published - 2017

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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10.1039/c7ra07128k

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Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines. / Bandi, Vijayalakshmi; Kavala, Veerababurao; Hsu, Che Hao; Konala, Ashok; Villuri, Bharath Kumar; Kotipalli, Trimurtulu; Kuo, Chun Wei; Yao, Ching Fa.

In: RSC Advances, Vol. 7, No. 74, 2017, p. 46704-46712.

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

Bandi, Vijayalakshmi ; Kavala, Veerababurao ; Hsu, Che Hao ; Konala, Ashok ; Villuri, Bharath Kumar ; Kotipalli, Trimurtulu ; Kuo, Chun Wei ; Yao, Ching Fa. / Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines. In: RSC Advances. 2017 ; Vol. 7, No. 74. pp. 46704-46712.

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title = "Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines",

abstract = "An approach for the synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives is reported starting from β-halo styrene and phenyl acetylene derivatives in the presence of PdCl2 and CuI catalysts. Functional groups such as aldehyde, cyano and ester groups are well tolerated and afford the desired functionalized dienynes. Further, these 1,3-buta-diene-3-yne derivatives are utilized for the synthesis of novel trisubstituted pyridine derivatives.",

author = "Vijayalakshmi Bandi and Veerababurao Kavala and Hsu, {Che Hao} and Ashok Konala and Villuri, {Bharath Kumar} 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 HRMS, NMR spectral and Crystallographic data respectively. Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7ra07128k",

language = "English",

volume = "7",

pages = "46704--46712",

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AU - Bandi, Vijayalakshmi

AU - Kavala, Veerababurao

AU - Hsu, Che Hao

AU - Konala, Ashok

AU - Villuri, Bharath Kumar

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 HRMS, NMR spectral and Crystallographic data respectively. Publisher Copyright: © 2017 The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - An approach for the synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives is reported starting from β-halo styrene and phenyl acetylene derivatives in the presence of PdCl2 and CuI catalysts. Functional groups such as aldehyde, cyano and ester groups are well tolerated and afford the desired functionalized dienynes. Further, these 1,3-buta-diene-3-yne derivatives are utilized for the synthesis of novel trisubstituted pyridine derivatives.

AB - An approach for the synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives is reported starting from β-halo styrene and phenyl acetylene derivatives in the presence of PdCl2 and CuI catalysts. Functional groups such as aldehyde, cyano and ester groups are well tolerated and afford the desired functionalized dienynes. Further, these 1,3-buta-diene-3-yne derivatives are utilized for the synthesis of novel trisubstituted pyridine derivatives.

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Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines

Abstract

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CCDC 1557912: Experimental Crystal Structure Determination

CCDC 1557911: Experimental Crystal Structure Determination

CCDC 1556914: Experimental Crystal Structure Determination

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Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines

Abstract

ASJC Scopus subject areas

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Other files and links

Fingerprint

Datasets

CCDC 1557912: Experimental Crystal Structure Determination

CCDC 1557911: Experimental Crystal Structure Determination

CCDC 1556914: Experimental Crystal Structure Determination

Cite this