Marco Pocci

1,3-Dithiane polymers for the supported synthesis of ketones

Abstract The synthesis of polymeric reagents containing an odourless propane-1,3-dithiol functionality is reported. Their usefulness for the solid phase synthesis of ketones via the umpoled alkylation of 1,3-dithianes is demonstrated.

Unexpected behavior of the methoxymethoxy group in the metalation/formylation reactions of 3-methoxymethoxyanisole

The formation of tetrasubstituted benzenes and doubly lithiated intermediates in metalation/formylation reactions of 3-methoxymethoxyanisole has been observed with the methoxymethoxy group acting as a leaving group in some cases.

Vinyl monomers containing 1,2-thia-, selena- and tellurazole systems, their polymers and copolymers

Synthese de ces monomeres, homopolymerisation radicalaire et copolymerisation avec le styrene

3,4-(Methylenedioxy)benzyl acrylate/acrylic acid copolymers as selective pH-controlled flocculants for finely divided titanium minerals

Abstract Fully synthetic tailor-made radical copolymers of 3,4-(methylenedioxy)benzyl acrylate with acrylic acid afforded excellent pH-controlled selective flocculation of aqueous ultrafine dispersions of the titanium minerals rutile and ilmenite. Sedimentation experiments proved that the copolymers, characterized by osmotic molecular weights in the range of 35 000–476 000 Da, produced stable, well separable flocs with rutile or ilmenite at acidic pH while they did not flocculate gangue minerals such as quartz. They showed the distinctive, very useful property of reversibly changing their effect from flocculation to dispersion or neutral by changing the pH. The formation of flocs is interpreted on the basis of a preliminary gathering process of the particles determined by the pH-dependent alteration of the particle surface solvation carried out with the copolymer.

New synthesis of 1,2,5-selenadiazoles

Synthese par reaction de thiadiazole-1,2,5 ou de derives monosubstitues avec un reactif de Grignard puis le melange SeCl 4 /Se (correspondant a SeCl)

Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases

In order to obtain substrate-like inhibitors of copper amine oxidases (CAOs), a class of enzymes involved in important cellular processes as well as in crosslinking of elastin and collagen and removal of biogenic primary amines, we synthesized a set of benzylamine derivatives properly substituted at positions 2 and 6 and studied their biological activity towards some members of CAOs. With benzylamines 6, 7, 8 containing linear alkoxy groups we obtained reversible inhibitors of benzylamine oxidase (BAO), very active and selective toward diamine oxidase (DAO), lysyl oxidase (LO) and monoamine oxidase B (MAO B) characterized by a certain toxicity consequent to the crossing of the brain barrier. Poorly toxic, up to very active, reversible inhibitors of BAO, very selective toward DAO, LO and MAO B, were obtained with benzylamines 10, 11, 12 containing hydrophilic ω-hydroxyalkoxy groups. With benzylamines 13, 14, 15, containing linear alkyl groups endowed with steric, but not conjugative effects for the absence of properly positioned oxygen atoms, we synthesized moderately active inhibitors of BAO reversible and selective toward DAO, LO and MAO B. The cross examination of the entire biological data brought us to the conclusion that the bioactive synthesized compounds most likely exert their physiological role of reversible inhibitors in consequence of the formation of a plurality of hydrogen bonds or hydrophobic non-covalent interactions with proper sites in the protein. Accordingly, the reported inhibitors may be considered as a set of research tools for general biological studies and the formation of enzyme complexes useful for X-ray structure determinations aimed at the design of more sophisticated inhibitors to always better modulate the protein activity without important side effects.

Synthesis of Model Molecules and NMR Analysis of Polymeric Reagents Based on Propane‐1,3‐dithiol and 1,3‐Dithiane Systems

Purposely synthesized model compounds, one- and two-dimensional NMR spectra and simulations are used for a full 1H and 13C NMR spectroscopic investigation of soluble copolymeric reagents for supported organic syntheses containing (1,3-propanediyl)bis(benzenesulfonate), (1,3-propanediyl)bis(thioacetate), propane-1,3-dithiol, and 1,3-dithiane functions. The collected NMR spectroscopic data confirm the possibility of rapid and accurate assessments of preparations and applications of the newly prepared copolymeric reagents, without resorting to special equipment.

Monomers, polymers, copolymers, resins, and coated silicas containing benzylamine residues planned as artificial substrates of benzylamine oxidase

The new monomers 3-(3-methacryloxypropoxy)benzylamine and 4-(3-methacryloxypropoxy)benzylamine in the form of hydrochlorides have been synthesized and radically copolymerized under various conditions with comonomers of different hydrophilicity, including N-acryloylmorpholine, N-acryloylpyrrolidine, N,N-dimethylacrylamide, and N-vinylbenzoylmorpholine, to obtain linear soluble, granular crosslinked, and silica-based macromolecular systems designed for investigating the action mechanism of benzylamine oxidase. Some characteristics of the prepared materials, including scanning electron microscopy photographs, are reported.

New 2,3-dihydro-5h-1,4-benzodioxepin derivatives. Easy formation and x-ray structure determination of a pentacyclic acetal containing a fourteen-membered carbon-oxygen ring

Abstract The acid catalyzed acetalization of 2,6-bis(2-hydroxyethoxy)benzaldehyde ( 4 ) is studied under various conditions. New 2,3-dihydro-5 H -1,4-benzodioxepin derivatives are prepared and a fourteen-membered tetraoxy-genated macrocycle is obtained in 81% yield without special synthetic expedients. The solid state molecular structure of the macrocyclic compound is determined by single crystal X-ray analysis.

Synthesis and NMR investigation of styrene glycopolymers containing D-galactose units functionalized with 4-(4-hydroxybutoxy)benzylamine residues

As a part of a work aimed at the synthesis of properly functionalized nanostructured glycopolymers suitable for interaction studies with copper amine oxidases, D-galactose was transformed through a six step sequence into the monomer N-(4-vinylbenzoyl)-6-amino-6-deoxy-D-galactose (1) which was converted into nanostructured crosslinked polymers (R1) by radical precipitation polymerization and into linear polymers (P1) by solution polymerization. The linear polymers were useful models for setting up glycosylation reactions to introduce N-trifluoroacetyl-4-(4-hydroxybutoxy)benzylamine residues in the presence of camphor sulfonic acid as the catalyst and to extend them to the nanostructured systems. The advancement of the glycosylation reaction was performed through the synthesis and glycosylation of N-benzoyl-6-amino-6-deoxy-D-galactose (9) as the model molecule for accurate NMR investigations. The removal of the trifluoroacetyl protecting group, unexpectedly stable, in glycosylated P1 and R1 was achieved with sodium borohydride.