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Authors
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Gube, A. ; Komber, H. ; Sahre, K. ; Friedel, P. ; Voit, B. ; Böhme, F.
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Title
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Formation of oligomeric and macrocyclic ureas based on 2,6-diaminopyridine
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Date
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08.11.2012
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Number
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34183
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Abstract
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The conversion of 1,3-bis-(6-amino-pyridin-2-yl)-urea (1) with N,N'-carbonyldiimidazole at high temperatures in DMSO yielded a mixture of defined cyclic trimers and tetramers. On the basis of model reactions, exchange reactions were evidenced, which convert the cyclic tetramer into a stable cyclic trimer. Linear even numbered oligomers were obtained in acetone under reflux where side reactions were suppressed. The pronounced tendency of cyclization is attributed to a preferred folded conformation of the urea bond between two pyridyl units.
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Publisher
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Journal of Organic Chemistry
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Wikidata
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Citation
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Journal of Organic Chemistry 77 (2012) 9620-9627
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DOI
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https://doi.org/10.1021/jo3015598
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Tags
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oligopyridine-dicarboxamide strands single helical structures oligo(phenanthroline dicarboxamide)s heterocyclic ureas foldamers naphthyridine system amide
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