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Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9-Diethylfluorene (Part I).

ABSTRACT: 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 -CH₂-, -CH₂NHCH₂- or -CH₂N=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.

SUBMITTER: Seidel P

PROVIDER: S-EPMC7689417 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9-Diethylfluorene (Part I).

Seidel Pierre P Mazik Monika M

ChemistryOpen 20201126 11

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 -CH2-, -CH2NHCH2- o ...[more]

PMID: 33304735

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Dataset Information

Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9-Diethylfluorene (Part I).

Publications

Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9-Diethylfluorene (Part I).

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