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Authors: STEFANIA IONESCU-ZINCA, PEDRO LAMEIRAS, DAN PORUMB, EMESE GÁL, MIRCEA DARABANTU.
DOI: 10.24193/subbchem.2020.1.04
Published Online: 2020-03-30
Published Print: 2020-03-30
pp. 39-54
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Starting from etheric type derivatives of 4-aminophenol, namely (4-aminophenoxy)acetic acid or 4-(4-aminophenoxy)butyric acid and 4-(n-octyloxy)aniline, we report herein two routes of access to two novel N-substituted amphionic melamines with the tandem 4-(1-carboxy-n-alkoxy) phenyl/4-(n-octyloxy)phenyl units against the piperazin-1-yl group, as a basic site. The successful SN2-Ar aminations of cyanuric chloride performed with these amine-nucleophiles are discussed in terms of chemoselectivity, mainly in the third step of the synthesis, implying piperazine as such or its N-Boc-mono-protected form. The amphionic nature of the targeted melamines was fully confirmed both in solution (VT-NMR) and in the solid state (IR).
Keywords: (4-aminophenoxy)acetic acid, 4-(4-aminophenoxy)butyric acid, amphionic melamines, N-Boc-piperazine, 4-(n-octyloxy)aniline.
