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

Research output: Contribution to journalArticle

14 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 languageEnglish
Pages (from-to)1841-1848
Number of pages8
JournalTetrahedron
Volume69
Issue number7
DOIs
Publication statusPublished - 2013 Feb 18

Fingerprint

Sodium Azide
Azides
Anions
Copper
Catalysts
Derivatives
benzofuran

Keywords

  • Chromenes
  • Chromenotetrazoles
  • Copper iodide
  • Cyanobenzofurans

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Gawande, S. D., Raihan, M. J., Zanwar, M. R., Kavala, V., Janreddy, D., Kuo, C. W., ... Yao, C-F. (2013). The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide. Tetrahedron, 69(7), 1841-1848. https://doi.org/10.1016/j.tet.2012.12.062

The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide. / Gawande, Sachin D.; Raihan, Mustafa J.; Zanwar, Manoj R.; Kavala, Veerababurao; Janreddy, Donala; Kuo, Chun Wei; Chen, Mei Ling; Kuo, Ting Shen; Yao, Ching-Fa.

In: Tetrahedron, Vol. 69, No. 7, 18.02.2013, p. 1841-1848.

Research output: Contribution to journalArticle

Gawande, SD, Raihan, MJ, Zanwar, MR, Kavala, V, Janreddy, D, Kuo, CW, Chen, ML, Kuo, TS & Yao, C-F 2013, 'The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide', Tetrahedron, vol. 69, no. 7, pp. 1841-1848. https://doi.org/10.1016/j.tet.2012.12.062
Gawande SD, Raihan MJ, Zanwar MR, Kavala V, Janreddy D, Kuo CW et al. The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide. Tetrahedron. 2013 Feb 18;69(7):1841-1848. https://doi.org/10.1016/j.tet.2012.12.062
Gawande, Sachin D. ; Raihan, Mustafa J. ; Zanwar, Manoj R. ; Kavala, Veerababurao ; Janreddy, Donala ; Kuo, Chun Wei ; Chen, Mei Ling ; Kuo, Ting Shen ; Yao, Ching-Fa. / The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide. In: Tetrahedron. 2013 ; Vol. 69, No. 7. pp. 1841-1848.
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