Design, synthesis and structure of new dendritic melamines. First use of a tandem C-2-substituted serinol¡ªO,O-masked 4-piperidone as a peripheral unit in iterative synthesis

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• 作者：Flavia Popa ; Pedro Lameiras ; Oana Moldovan ; Maria Tomoaia-Cotisel ; Eric Henon ; Agathe Martinez ; Carmen Sacalis ; Aurora Mocanu ; Yvan Ramondenc ; Mircea Darabantu
• 关键词：Dendrimers ; Melamines ; Serinols ; 4-Piperidone ; NMR ; AFM (atomic force microscopy)
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：28 October, 2012
• 年：2012
• 卷：68
• 期：43
• 页码：8945-8967
• 全文大小：3877 K

文摘

The iterative chemoselective amination of cyanuric chloride to dimers of new G-2 dendritic N-substituted-2,4,6-triamino-s-triazines (melamines) having C-2-substituted 2-aminopropane-1,3-diols (¡®serinols¡¯) in tandem with the ethylene ketal of 4-piperidone as peripheral units is reported. The structure as a function of increasing molecular size was studied by NMR spectroscopy, DFT calculation and AFM imaging. A concise nomenclature defining the restricted rotational phenomena about the newly created C(s-triazine)-N(exocyclic) partial double bonds, seen as axes of (pro)diastereomerism, is used. We propose a new form of frontier rotamerism for the dendrimer surface, which operates over a long range.