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Application of one-pot synthesis of Cu(I)-catalyzed cycloaddition between azides and terminal alkynes : a new one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal acetylenes and in situ generated azides

Høydahl, Edmund Andre
Master thesis
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Year
2006
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http://urn.nb.no/URN:NBN:no-14735

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  • Farmasøytisk institutt [1340]
Abstract
Abstract

Multi-component reactions are a very elegant and rapid way to access highly functional molecules from simple building blocks in drug lead synthesis. Multi-component one-pot reactions generally afford good yields which is important in combinatorial synthesis. Over the past decade, several sequential multi-component reactions have been developed into multi-component one-pot reactions. Since multi-component one-pot reactions results in a reduced number of operations, they usually allows direct transformation of intermediates to desired products by avoiding isolation, handling and chromatography. Hence, better yields are usually achieved.

In this study 1,4-disubstituted 1,2,3-triazoles were obtained by a high-yielding copper (I) catalyzed 1,3-dipolar cycloaddition reaction between in situ generated azides and terminal acetylenes. This one-pot, two-step procedure tolerated most functional groups and circumvented the problems associated with the isolation of potentially toxic and explosive organic azides. All of these factors are important in combinatorial synthesis of drug lead compounds.
 
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