Open AccessSyntheses of Acyclic and Macrocyclic Compounds Derived from 9,9‐Diethylfluorene (Part I)
Author(s) -
Seidel Pierre,
Mazik Monika
Publication year - 2020
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.202000268
Subject(s) - chemistry , fluorene , yield (engineering) , pyridinium , stereochemistry , biphenyl , medicinal chemistry , organic chemistry , polymer , materials science , metallurgy
A series of new 9,9‐diethylfluorenes consisting of three side‐arms each bearing a heterocyclic, bis(carboxymethyl)amino, bis(carbamoylmethyl)amino, bis(ethoxycarbonylmethyl)amino or an amino group were prepared on the basis of 2,4,7‐tris(bromomethyl)‐9,9‐diethylfluorene. Imidazolyl, benzimidazolyl, pyrazolyl, pyrrolyl, 1,3‐dioxoisoindolyl and pyridinium groups were taken into account as heterocyclic units, attached to the aromatic skeleton via −CH 2 −, −CH 2 NHCH 2 − or −CH 2 N=CH− linkers. In addition to the seventeen 2,4,7‐trisubstituted 9,9‐diethylfluorenes, two macrocyclic compounds were prepared on the basis of 2,7‐bis(aminomethyl)‐9,9‐diethylfluorene. The excellent yield of the macrocyclization reaction is worth a special mention. Both the acyclic and the macrocyclic fluorene‐based compounds have, among other things, the potential to act as artificial receptors for different substrates in analogy to the known receptors consisting of a benzene or biphenyl core.