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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 10
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Original Articles

Synthesis of Novel Glycoconjugates Derived From Alkynyl Heterocycles through a Click Approach

, , , &
Pages 1432-1438 | Received 21 Oct 2011, Published online: 05 Mar 2013
 

Abstract

The synthesis of a series of novel 1,4-disubstituted 1,2,3-triazole compounds bearing a D-glucose derivative and an heteroaromatic system is described. Alkylation of isatin, 3-methyl-carbazole, and one tetrahydro-γ-carboline with propargyl bromide gave their N-propargyl derivatives in good yields. These compounds further reacted with acetylated D-glucose with the azide group in position 1 to give three final products and with peracetylated 6-azido-6-deoxy-α-D-methylglucoside, giving the corresponding derivative of tetrahydro-γ-carboline.

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GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We gratefully acknowledge the financial support from FCT (Fundaçãopara a Ciência e Tecnologia) and FEDER for National NMR Network (Bruker Avance II 400) and REEQ/630/QUI/2005 (LC/MS instrument).

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