Intermolecular 1,3-dipolar cycloadditions of azomethine imines

Dipolar cycloadditions of azomethine imines, formed in situ from aldehydes and N1-alkyl-N2-acylhydrazines, with electron-deficient dipolarophiles produce pyrazolidines: mono-substituted dipolarophiles afford principally 4-substituted pyrazolidines

An alkylation route to carbo- and heteroaromatic amino acids

Amino acids carrying aromatic carbo- and heterocycles in the side chain, such as naphthyl-, biphenyl- and pyridylalanines, have been prepared by alkylation of a glycine enolate with a haloalkyl carbocycle or heterocycle, with enantiomeric excess up to 87% using the ephedrine amide protocol

Synthesis of some new 2-heterosubstituted 4,5-dihydroimidazoles

Several new 4,5-dihydroimidazoles (and the corresponding imidazolium salts) carrying heteroatom substituents at C-2 have been prepared from the corresponding tetrahydroimidazol-2-ones and/or -thiones

A catalytic dipolar cycloaddition route to pyrroloimidazoles

A catalytic method involving carbenoid insertion onto dihydroimidazoles is reported for the generation of dihydroimidazolium ylides, and their subsequent diastereoselective cycloaddition to form pyrrolo[1,2-a]imidazole

Synthesis by conjugate radical addition of new heterocyclic amino acids with nucleobase side chains

N-(2-Iodoethyl) and N-(3-iodopropyl)pyrimidines and purines undergo stereoselective conjugate radical addition with an optically active oxazolidinone acceptor to give syn adducts that can be converted into amino acids carrying pyrimidine and purine (nucleobase) side chains

New methodologies for the synthesis of 3-acylpyridone metabolites

A core isoxazolo[4,3-c]pyridin-4-one scaffold is prepared and elaborated at C-3(Me) and C-7 as a masked building block for 3-acylpyridin-2-ones related to the acylpyridone natural products

Tetraplex DNA specific ligands based on the fluorenone-carboxamide scaffold

A series of fluorenone-carboxamide compounds was analyzed with regard to DNA binding properties by UV spectroscopy and competition dialysis methods. The morpholino derivative 10 provided interesting results in terms of affinity and specificity toward the DNA G-tetraplex structures. Interactions against this target were evaluated by a comparative molecular modeling study in agreement with the experimental data, proposing a model for the rational design of new agents with potent and selective DNA tetraplex binding properties

Monofluorinated di- and tetrahydropyrans via Prins-type cyclisations

The synthesis of a range of fluorinated heterocycles is described via a Lewis acid-mediated Prins-type cyclisatio

Aldol elaboration of 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-ones, masked precursors to acylpyridones

A core 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine-4-one scaffold is elaborated at C-3(Me) by base-mediated aldol condensation to give new 3-alkenyl-4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine-4-ones, which are masked forms related to the acylpyridone natural products