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Amino Surface‐Functionalized Tris(calix[4]arene) Dendrons with Rigid C 3 ‐Symmetric Propeller Cores
Author(s) -
Gattuso Giuseppe,
Grasso Giulia,
Marino Nino,
Notti Anna,
Pappalardo Andrea,
Pappalardo Sebastiano,
Parisi Melchiorre F.
Publication year - 2011
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.201100812
Subject(s) - chemistry , tris , amine gas treating , amide , polymer chemistry , catalysis , covalent bond , dendrimer , medicinal chemistry , stereochemistry , organic chemistry , biochemistry
Abstract Dendrons composed of three functionalized cone calix[4]arene substructures covalently bound to rigid C 3 ‐symmetric tris‐anilino cores through amide linkages have been obtained by a divergent synthetic protocol involving the coupling of p ‐nitrocalix[4]arene butanoic acid 9 with tris(4‐aminophenyl)amine ( TAPA ), 1,3,5‐tris(4‐aminophenyl)benzene ( TAPB ), and 2,4,6‐tris(4‐aminophenyl)‐ s ‐triazine ( TAPT ). Two different amidation procedures were used to generate the dodecanitro intermediates (through activation of acid 9 with PyBOP catalyst or transformation into its acid chloride). The final reduction to the title dodecaamino dendrons was smoothly carried out with H 2 and Raney‐Ni catalyst.