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The hydrogenation of heterocyclic calix[4]arenes, a transformation leading to novel macrocyclic ligands

2012, Journot, Guillaume, Jones, Christopher R., Blangy, Valeria, Neier, Reinhard

A review. Hydrogenation reactions of calix[4]furan and calix[4]pyrrole were reviewed together with the authors' own work in this field. A short description of the metal binding process of our new calix[4]pyrrolidines (= the fully satd. calix[4]pyrrole) with Cu was discussed as a typical example of the metal binding capacities. The new calix[4]pyrrolidines can be structurally classified as new stiffened macrocyclic crown ethers or as satd. analogs of the porphyrin-derived "pigments of life". [on SciFinder(R)]

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Synthesis, structure, and complexation properties of partially and completely reduced meso-octamethylporphyrinogens (calix[4]pyrroles)

2009, Blangy, Valeria, Heiss, Christoph, Khlebnikov, Vsevolod, Letondor, Christophe, Stoeckli-Evans, Helen, Neier, Reinhard

Calixpyrroles bind anions efficiently and can be transformed into transition-metal complexes only under forcing conditions. Reducing the macrocycle creates a ligand that easily forms classical Werner complexes with Cu, Ni, and Pd ions. The metal complexes present an array of four directed H bonds, which specifically bind the counterions. [on SciFinder(R)]

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N,O- and N,S-ketene acetals as substrates for aza-Claisen rearrangement

1998, Neuschutz, Klaus, Fernandez, Jimena, Simone, Jean-Mary, Neier, Reinhard

N,O-ketene acetals and N,S-ketene with a benzoyl group on the nitrogen are more stable than ketene acetals with a benzyl group on the nitrogen. These compds. undergo an aza-Claisen rearrangement. Due to high temps. and long reaction times needed, yields from N,O-ketene acetals are poor. N,S-ketene acetals are more stable than N,O-acetals, and temp. requirements to effect rearrangement are even higher. Catalysis, though attempted, could not be achieved. [on SciFinder(R)]

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An Efficient Photoinduced Deprotection of Aromatic Acetals and Ketals

2011, Thevenet, Damien, Neier, Reinhard

A novel type of photodeprotection reaction of simple arom. acetals and ketals is described. The deprotection is highly efficient under optimized conditions. The arom. ring confers the photoreactivity to the compds. The efficiency of the process depends on the structure of the acetal moiety. The common minor side reaction, the photooxidn., becomes the major reaction pathway in the case of cyclic acetals. The use of photon as only reagent makes this procedure esp. attractive for acetal deprotection. [on SciFinder(R)]

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Novel bioconjugates of aminolevulinic acid with nucleosides

2008, Gurba, Patrice, Vallinayagam, Ramakrishnan, Schmitt, Frederic, Furrer, Julien, Juillerat-Jeanneret, Lucienne, Neier, Reinhard

Esters and amino acid derivs. of 5-aminolevulinic acid (ALA) are efficient prodrugs for the prodn. of protoporphyrin IX (PpIX), which has been used in photodynamic cancer therapy (PDT). The synthesis of novel bioconjugates, e.g. I·CF3CO2H, combining ALA with adenosine and thymidine is reported. The novel bioconjugates have been made using a robust methodol. The new class of prodrugs contains one, two, or three ALA per mol. Preliminary cell tests in human cancer cell lines indicate that the thymidine conjugate of ALA is an efficient prodrug for PDT. [on SciFinder(R)]

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Synthesis and characterization of ?-extended porphyrins as potential precursors for the formation of columnar mesophases: design principles for columnar mesophases need revision?

2011, Herzog, Beat, Neier, Reinhard

Meso-? bridged extended porphyrins substituted with long aliph. chains were synthesized and fully characterized. Two different synthetic strategies were tested to obtain the target structures. The synthetic steps were optimized to obtain scalable routes for the prodn. of sufficient quantities of ?-extended porphyrins for material science studies. The porphyrins were obtained either as free bases or complexed with NiII or CuII. UV-visible spectroscopy and polarized light microscopy was used for the anal. of the material properties of the ?-extended porphyrins. The results obtained with the authors' compds. are not compatible with the results reported in the literature. [on SciFinder(R)]

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Science of Synthesis, Volume 12, Houben-Weyl Methods of Molecular Transformations; Hetarenes and Related Ring Systems. Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms

2002, Neier, Reinhard