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Unusual Anisotropic Effects from 1,3-Dipolar Cycloadducts of 4-Azidomethyl Coumarins

Kusanur, Raviraj A and Kulkarni, Manohar V and Kulkarni, Geetha M and Nayak, Susanta K and Row, Tayur N Guru and Ganesan, Kilivelu and Sun, Chung-Ming (2010) Unusual Anisotropic Effects from 1,3-Dipolar Cycloadducts of 4-Azidomethyl Coumarins. In: Journal of Heterocyclic Chemistry, 47 (1). pp. 91-97.

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Official URL: http://www3.interscience.wiley.com/journal/1232275...


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 pi-electrons of the triazole ring, further supported by diffraction and computational studies.

Item Type: Journal Article
Publication: Journal of Heterocyclic Chemistry
Publisher: Journal of Heterocyclic Chemistry
Additional Information: Copyright of this article belongs to Journal of Heterocyclic Chemistry.
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 08 Mar 2010 12:40
Last Modified: 08 Mar 2010 12:40
URI: http://eprints.iisc.ac.in/id/eprint/25902

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