Synthesis of Regio- and Stereoisomers of Highly Functionalized 1,2,3- Triazole-substituted Cyclopentanes

Author(s): Lorand Kiss, Eniko Forro, Ferenc Fulop

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 3 , 2011

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Highly functionalized regio- and stereoisomers of 1,2,3-triazole-substituted cyclopentanes were prepared in six steps from either bicyclic β-lactam 7 or γ-lactam 23 by 1,3-dipolar cycloaddition of the azido cyclopentanol intermediates with acetylenes. The reactions of azido aminocyclopentanols with non-symmetric acetylenes resulted regioselectively in the corresponding 1,4-disubstitued triazole derivatives under both thermal and Cu(I)-catalysed conditions. These compounds can be regarded as highly functionalized 1,2,3-triazole-modified carbocyclic nucleoside analogues.

Keywords: Amino alcohols, azides, carbocyclic nucleosides, click chemistry, 1,3-dipolar cycloaddition, enzymes, 1,2,3- triazoles, antiviral activity, Triazole-modified, multifunctionalized cyclopentanes

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Article Details

Year: 2011
Page: [220 - 228]
Pages: 9
DOI: 10.2174/157017811795038359
Price: $65

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