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

16 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

Keywords

  • Chromenes
  • Chromenotetrazoles
  • Copper iodide
  • Cyanobenzofurans

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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