A one-step procedure for the selective trifluoroacetylation of primary amino groups of polyamines

O’Sullivan, Mary C.; Dalrymple, Damon M.

doi:10.1016/0040-4039(95)00630-u

Cited by 75 publications

(32 citation statements)

References 15 publications

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“…The mono-Boc-protected norspermidine 20 was prepared from norspermidine via intermediates 16 and 19 by using a reported procedure (Scheme 6). [15] Tetra-alA C H T U N G T R E N N U N G kyl-A C H T U N G T R E N N U N G aA C H T U N G T R E N N U N G tion with bromopropylphthalimide in the presence of potassium carbonate in acetonitrile at reflux gave tertiary amine 21. The subsequent cleavage of the Boc group was carried out at 0 8C with TFA in chloroform to give compound 22 in almost quantitative yield.…”

Section: Resultsmentioning

confidence: 99%

Design and Photophysical Properties of Zinc(II) Porphyrin‐Containing Dendrons Linked to a Central Artificial Special Pair

Brégier

Aly

Gros

et al. 2011

Chemistry A European J

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The click chemistry synthesis and photophysical properties, notably photo-induced energy and electron transfers between the central core and the peripheral chromophores of a series of artificial special pair-dendron systems (dendron = G1, G2, G3; Gx = zinc(II) tetra-meso-arylporphyrin-containing polyimides) built upon a central core of dimethylxanthenebis(metal(II) porphyrin) (metal = zinc, copper), are reported. The dendrons act as singlet and triplet energy acceptors or donors, depending on the dendrimeric systems. The presence of the paramagnetic d(9) copper(II) in the dendrimers promotes singlet-triplet energy transfer from the zinc(II) tetra-meso-arylporphyrin to the bis(copper(II) porphyrin) unit and slow triplet-triplet energy transfer from the central bis(copper(II) porphyrin) fragment to the peripheral zinc(II) tetra-meso-arylporphyrin. If bis(zinc(II) porphyrin) is the central core, evidence for chain folding is observed; this is unambiguously demonstrated by the presence of triplet-triplet energy transfer in the heterobimetallic systems, a process that can only occur at short distances.

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Section: Resultsmentioning

confidence: 99%

Design and Photophysical Properties of Zinc(II) Porphyrin‐Containing Dendrons Linked to a Central Artificial Special Pair

Brégier

Aly

Gros

et al. 2011

Chemistry A European J

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“…During this procedure, overreaction was avoided by preferential protonation of the secondary amine, [5] leading to compound 3 in nearly quantitative yield (97 %).…”

Section: Resultsmentioning

confidence: 99%

A New Robust and Versatile Tetradentate Linker for Amides To be Cleaved under Mild Conditions by Unusual Complexation of the Amide Nitrogen to Cu⁺⁺

et al. 2009

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The concept of weakening amide bonds by the rather unusual forced complexation of nitrogen to Cu++ is not limited to tridentate ligands and was extended in this work to tetradentate ligands as well. The use of cyclic tetradentate ligands was to no avail, but an open‐chain and more‐flexible tetradentate ligand allowed mild cleavage by methanolysis after complexation. The principle was applied to the development of a new linker for solid‐phase chemistry, which was proven to be extremely robust, yet allowed mild cleavage after activation by Cu++ complexation. Its stability and versatility was demonstrated by the successful application to a whole plethora of different types of reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…1 shows the steps in the reaction for the synthesis of these N 4 ,N 9 -disubstituted spermines. In 1995, two research groups independently reported the selective protection of a primary amine as its trifluoroacetamide by reaction with ethyl trifluoroacetate (40,41). When we developed this strategy in our homologation of polyamines for the rapid, practical synthesis of lipospermines and related lipoplexes (42), we assumed that the higher nucleophilicity of the secondary amines is masked by correspondingly powerful steric effects.…”

Section: Synthesis Of Lipospermines (N 4 N 9 -Disubstituted Sperminementioning

confidence: 98%

Very Long Chain N 4 ,N 9 -Diacyl Spermines: Non-Viral Lipopolyamine Vectors for Efficient Plasmid DNA and siRNA Delivery

Ghonaim

Blagbrough

2008

Pharm Res

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A one-step procedure for the selective trifluoroacetylation of primary amino groups of polyamines

Cited by 75 publications

References 15 publications

Design and Photophysical Properties of Zinc(II) Porphyrin‐Containing Dendrons Linked to a Central Artificial Special Pair

Design and Photophysical Properties of Zinc(II) Porphyrin‐Containing Dendrons Linked to a Central Artificial Special Pair

A New Robust and Versatile Tetradentate Linker for Amides To be Cleaved under Mild Conditions by Unusual Complexation of the Amide Nitrogen to Cu⁺⁺

Very Long Chain N 4 ,N 9 -Diacyl Spermines: Non-Viral Lipopolyamine Vectors for Efficient Plasmid DNA and siRNA Delivery

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A one-step procedure for the selective trifluoroacetylation of primary amino groups of polyamines

Cited by 75 publications

References 15 publications

Design and Photophysical Properties of Zinc(II) Porphyrin‐Containing Dendrons Linked to a Central Artificial Special Pair

Design and Photophysical Properties of Zinc(II) Porphyrin‐Containing Dendrons Linked to a Central Artificial Special Pair

A New Robust and Versatile Tetradentate Linker for Amides To be Cleaved under Mild Conditions by Unusual Complexation of the Amide Nitrogen to Cu++

Very Long Chain N 4 ,N 9 -Diacyl Spermines: Non-Viral Lipopolyamine Vectors for Efficient Plasmid DNA and siRNA Delivery

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A New Robust and Versatile Tetradentate Linker for Amides To be Cleaved under Mild Conditions by Unusual Complexation of the Amide Nitrogen to Cu⁺⁺