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Synthesis of new beta-amidodehydroaminobutyric acid derivatives and of new tyro...

Several beta-amidodehydroaminobutyric acid derivatives were prepared from N,C-diprotected beta-bromodehydroaminobutyric acids and amides by a copper catalyzed C-N coupling reaction. The best reaction conditions include the use of a catalytic amount of CuI, N,N’-dimethylethylenediamine as ligand and K2CO3 as base in toluene at 110 ºC. The stereochemistry of the products was determined using NOE difference experi...

Synthesis of fluorescent alanines by a rhodium catalysed conjugate addition of ...

Several arylalanine derivatives containing fluorescent groups were prepared in good yields using a rhodium catalysed conjugate addition of arylboronic acids to N,N-diprotected and N-monoprotected dehydroalanines. The best conditions for these reactions require the use of an excess of aryl boronic acid (4 equiv.), [Rh(COD)2]BF4 as catalyst and CsF as base in dioxane:H2O (10:1) at 110 ºC. These conditions were al...

Synthesis of 2,6-bis-(oxazolyl)pyridine ligands for luminescent Ln(III) complexes

Submitted to the European Journal of Organic Chemistry ; New bis-(oxazolyl)pyridine ligands for Ln(III) ions were prepared using a expeditious methodology from threonine and dipicolinic acid chloride. The synthetic strategy includes a dehydration step to give a bis-dehydroaminobutyric acid derivative followed by bromination and cyclization with DBU. Photophysical studies of Eu(III) and Tb(III) complexes of th...

Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes

Prova tipográfica ; A 3-(phenanthren-9-yl)-1H-indole-2-carboxylic acid (2) obtained from the cleavage of the methyl ester of the methyl 3-(phenanthren-9-yl)-1H-indole-2-carboxylate (1) was inserted into a peptide containing the RGD sequence. The GGRGDG peptide sequence was prepared by solid phase synthesis and coupled to compound (2), using diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) in DMF...

Synthesis of a new 2,6-bis-(oxazole)pyridine ligand as a sensitizer for lumines...

Electrochemical reduction of dehydroamino acids: Synthesis and photophysical pr...

Several beta,beta-disubstituted dehydroalanines were prepared from beta,beta-dibromo or beta-bromo, beta-substituted dehydroalanines and aryl boronic acids using a Suzuki-Miyaura cross-coupling reaction. The electrochemical behaviour of these compounds was studied by cyclic voltammetry. All compounds studied showed similar reduction potentials and these were similar to the peak potential of the methyl ester of ...

High yielding synthesis of oxazole-4-carboxylates from dehydroamino acid deriva...

Electrochemical reduction of β-Aryldehydroamino acid derivatives

Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes

Synthesis and photophysical studies of new fluorescent indole derivatives obtai...

Several new indole derivatives were synthesised from β-brominated dehydroamino acids and arylboronic acids by using a strategy developed in our research group that involves a sequential Suzuki–Miyaura cross-coupling reaction and a metal-assisted C–N intramolecular cyclisation. The cyclised products were obtained either by direct cyclisation or by isomerisation followed by cyclisation. The photophysical propert...