One-pot sequential azide–alkyne/intramolecular azomethine ylide 1,3-dipolar cycloaddition strategy for the synthesis of carbohydrate grafted macrocycles

[Display omitted] Synthesis of triazole linked macrocycles grafted with glyco-pyrrolidine/pyrrolizidine/thiazolidine/indolizine has been accomplished by one-pot sequential Huisgen cycloaddition and intramolecular azomethine ylide cycloaddition. The reaction involves the simultaneous formation of fiv...

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Bibliographic Details
Published in:Tetrahedron letters 2015-05, Vol.56 (21), p.2669-2673
Main Authors: Rao, J. Naga Siva, Raghunathan, R.
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
Azide–alkyne
Carbohydrates
Macrocycles
Triazole
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Summary:[Display omitted] Synthesis of triazole linked macrocycles grafted with glyco-pyrrolidine/pyrrolizidine/thiazolidine/indolizine has been accomplished by one-pot sequential Huisgen cycloaddition and intramolecular azomethine ylide cycloaddition. The reaction involves the simultaneous formation of five bonds in one-pot to construct complex chiral macrocycles from the easily available starting materials. The structures of the macrocycles were confirmed by spectroscopic methods and X-ray crystallographic analysis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.03.108