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Efficient Synthesis of 1,2,3‐Triazole‐Fused Bicyclic Compounds from Aldoses
Author(s) -
Dolhem Franck,
Al Tahli Fathia,
Lièvre Catherine,
Demailly Gilles
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500451
Subject(s) - chemistry , bicyclic molecule , cycloaddition , triazole , intramolecular force , monosaccharide , organic chemistry , stereochemistry , combinatorial chemistry , catalysis
We would like to report an expedient synthesis of 1,2,3‐triazole‐fused bicyclic compounds starting from naturally occurring carbohydrates. These imino sugars were prepared in four steps from glyco ‐ynitols, readily available from monosaccharides. The title compounds were prepared by intramolecular 1,3‐dipolar cycloaddition of azidoalkynes in a one‐pot substitution/thermal cyclization procedure. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)