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^*

^*Corresponding author for this work

Department of Chemistry

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

23 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1841-1848
Number of pages	8
Journal	Tetrahedron
Volume	69
Issue number	7
DOIs	https://doi.org/10.1016/j.tet.2012.12.062
Publication status	Published - 2013 Feb 18

Keywords

Chromenes
Chromenotetrazoles
Copper iodide
Cyanobenzofurans

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.12.062

Cite this

@article{156afaf56ba34713b0a45ae63bdc42d1,

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",

language = "English",

volume = "69",

pages = "1841--1848",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "7",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84872800594&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84872800594&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.12.062

DO - 10.1016/j.tet.2012.12.062

M3 - Article

AN - SCOPUS:84872800594

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 873992: Experimental Crystal Structure Determination

CCDC 880572: Experimental Crystal Structure Determination

CCDC 891973: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 873992: Experimental Crystal Structure Determination

CCDC 880572: Experimental Crystal Structure Determination

CCDC 891973: Experimental Crystal Structure Determination

Cite this