The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide

Sachin D. Gawande; Mustafa J. Raihan; Manoj R. Zanwar; Veerababurao Kavala; Donala Janreddy; Chun Wei Kuo; Mei Ling Chen; Ting Shen Kuo; Ching Fa Yao

doi:10.1016/j.tet.2012.12.062

The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide

Sachin D. Gawande, Mustafa J. Raihan, Manoj R. Zanwar, Veerababurao Kavala, Donala Janreddy, Chun Wei Kuo, Mei Ling Chen, Ting Shen 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

23 引文斯高帕斯（Scopus）

摘要

Two different roles of sodium azide under two different conditions are described here along with the plausible mechanisms. When sodium azide was treated with cyanochromenes under catalyst free conditions, the azide anion acted as a base. Hence, a base mediated rearrangement of cyanochromenes was resulted in formation of benzofuran derivatives. However, in the presence of catalytic amount of CuI the azide anion acted as a diene to produce chromenotetrazoles.

原文	英語
頁（從 - 到）	1841-1848
頁數	8
期刊	Tetrahedron
卷	69
發行號	7
DOIs	https://doi.org/10.1016/j.tet.2012.12.062
出版狀態	已發佈 - 2013 2月 18

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2012.12.062

其它文件與鏈接

CCDC 873992: Experimental Crystal Structure Determination
Gawande, S. D. (Creator), Raihan, M. J. (Creator), Zanwar, M. R. (Creator), Kavala, V. (Creator), Janreddy, D. (Creator), Kuo, C. (Creator), Chen, M. (Creator), Kuo, T. (Creator) & Yao, C. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccybg90, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccybg90&sid=DataCite
資料集: Dataset
CCDC 880572: Experimental Crystal Structure Determination
Gawande, S. D. (Creator), Raihan, M. J. (Creator), Zanwar, M. R. (Creator), Kavala, V. (Creator), Janreddy, D. (Creator), Kuo, C. (Creator), Chen, M. (Creator), Kuo, T. (Creator) & Yao, C. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccyk9kb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccyk9kb&sid=DataCite
資料集: Dataset
CCDC 891973: Experimental Crystal Structure Determination
Gawande, S. D. (Creator), Raihan, M. J. (Creator), Zanwar, M. R. (Creator), Kavala, V. (Creator), Janreddy, D. (Creator), Kuo, C. (Creator), Chen, M. (Creator), Kuo, T. (Creator) & Yao, C. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccyy5bc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccyy5bc&sid=DataCite
資料集: Dataset

引用此

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title = "The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide",

abstract = "Two different roles of sodium azide under two different conditions are described here along with the plausible mechanisms. When sodium azide was treated with cyanochromenes under catalyst free conditions, the azide anion acted as a base. Hence, a base mediated rearrangement of cyanochromenes was resulted in formation of benzofuran derivatives. However, in the presence of catalytic amount of CuI the azide anion acted as a diene to produce chromenotetrazoles.",

keywords = "Chromenes, Chromenotetrazoles, Copper iodide, Cyanobenzofurans",

author = "Gawande, {Sachin D.} and Raihan, {Mustafa J.} and Zanwar, {Manoj R.} and Veerababurao Kavala and Donala Janreddy and Kuo, {Chun Wei} and Chen, {Mei Ling} and Kuo, {Ting Shen} and Yao, {Ching Fa}",

note = "Funding Information: This work was supported by the National Science Council of the Republic of China ( NSC-100-2113-M-003-008-MY3 ) and National Taiwan Normal University ( 99T3030-2 , 99-D and 100-D-006 ) and Instrumentation Center at National Taiwan Normal University is gratefully acknowledged for providing spectral data. The authors are grateful to Professor Dr. Chen-Hsiung Hung of Academia Sinica for providing access to UV and Fluorescence instruments for obtaining the data presented in this paper. ",

year = "2013",

month = feb,

day = "18",

doi = "10.1016/j.tet.2012.12.062",

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T1 - The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide

AU - Gawande, Sachin D.

AU - Raihan, Mustafa J.

AU - Zanwar, Manoj R.

AU - Kavala, Veerababurao

AU - Janreddy, Donala

AU - Kuo, Chun Wei

AU - Chen, Mei Ling

AU - Kuo, Ting Shen

AU - Yao, Ching Fa

N1 - Funding Information: This work was supported by the National Science Council of the Republic of China ( NSC-100-2113-M-003-008-MY3 ) and National Taiwan Normal University ( 99T3030-2 , 99-D and 100-D-006 ) and Instrumentation Center at National Taiwan Normal University is gratefully acknowledged for providing spectral data. The authors are grateful to Professor Dr. Chen-Hsiung Hung of Academia Sinica for providing access to UV and Fluorescence instruments for obtaining the data presented in this paper.

PY - 2013/2/18

Y1 - 2013/2/18

N2 - Two different roles of sodium azide under two different conditions are described here along with the plausible mechanisms. When sodium azide was treated with cyanochromenes under catalyst free conditions, the azide anion acted as a base. Hence, a base mediated rearrangement of cyanochromenes was resulted in formation of benzofuran derivatives. However, in the presence of catalytic amount of CuI the azide anion acted as a diene to produce chromenotetrazoles.

AB - Two different roles of sodium azide under two different conditions are described here along with the plausible mechanisms. When sodium azide was treated with cyanochromenes under catalyst free conditions, the azide anion acted as a base. Hence, a base mediated rearrangement of cyanochromenes was resulted in formation of benzofuran derivatives. However, in the presence of catalytic amount of CuI the azide anion acted as a diene to produce chromenotetrazoles.

KW - Chromenes

KW - Chromenotetrazoles

KW - Copper iodide

KW - Cyanobenzofurans

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U2 - 10.1016/j.tet.2012.12.062

DO - 10.1016/j.tet.2012.12.062

M3 - Article

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SN - 0040-4020

VL - 69

SP - 1841

EP - 1848

JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -

The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 873992: Experimental Crystal Structure Determination

CCDC 880572: Experimental Crystal Structure Determination

CCDC 891973: Experimental Crystal Structure Determination

引用此