Expedient synthesis of coumarin-coupled triazoles via 'click chemistry' leading to the formation of coumarin–triazole–sugar hybrids

Kumar, K. Karthik ; Kumar, R. Mahesh ; Subramanian, V. ; Das, T. Mohan (2010) Expedient synthesis of coumarin-coupled triazoles via 'click chemistry' leading to the formation of coumarin–triazole–sugar hybrids Carbohydrate Research, 345 (16). pp. 2297-2304. ISSN 0008-6215

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.carres.2010.07.037

Abstract

Coumarin-based triazoles were synthesized from 3-azidomethylcoumarin and a terminal acetylenic compound. Uncatalysed thermal conditions result in a mixture of both 1,4- and 1,5-regioisomers or the thermodynamically more stable 1,4-regioisomer, whereas the Cu(I)-catalysed reaction affords only the favourable 1,4-regioisomer. B3LYP/6-31G(d) level of theory has been used to calculate geometry and frequency features of the reactants, transition states (TSs) and products. Computational studies further reveal that 1,4-regioisomeric products are more favourable and also thermodynamically more stable compared to the 1,5-regioisomers.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Coumarin Derivatives; Click Chemistry; Cu(I)-Catalysed; B3LYP/6-31G(d); Saccharide Triazole Derivative
ID Code:107656
Deposited On:01 Dec 2017 12:30
Last Modified:01 Dec 2017 12:30

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