Unusual anisotropic effects from 1,3-dipolar cycloadducts of 4-azidomethyl coumarins

Raviraj A. Kusanur, Manohar V. Kulkarni, Geetha M. Kulkarni, Susanta K. Nayak, Tayur N. Guru Row, Kilivelu Ganesan, Chung-Ming Sun

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

(Chemical Equation Presented) 4-Bromomethylcoumarins (1) reacted with sodium azide in aqueous acetone to give 4-azidomethyl-coumarins (2), which underwent 1,3-dipolar cycloaddition with acetylenic dipolarophiles to give triazoles (3). These triazoles (3) have been found to exhibit interesting variations in the chemical shifts of C 3 -H and C 4 -methylene protons. Protonation studies indicate that the shielding effect of the C 3 -H of coumarin is due to π-electrons of the triazole ring, further supported by diffraction and computational studies.

Original languageEnglish
Pages (from-to)91-97
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume47
Issue number1
DOIs
StatePublished - 12 Feb 2010

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