Search results for "Benzyl group"

Differential reactivity of fluorinated homopropargylic amino esters vs gold(I) salts. The role of the nitrogen protecting group

2015

The reaction of several homopropargyl amino esters 4, bearing aromatic substituents and a benzyl group as nitrogen substituents, with gold(I) salts gave rise to fluorinated quinolines 6 in a tandem hydroarylation-isomerization process. On the other hand, homopropargyl amino esters 7 containing a carbamate group underwent the carbonyl addition over the triple bond in the presence of gold(I) salts, rendering fluorinated oxazines 8. The use of chiral sulfoxides allowed us to develop the asymmetric version of this protocol. This two processes complete the differential reactivity showed by these types of susbtrates, depending on the nature of the nitrogen protecting group. (C) 2014 Elsevier B.V.…

Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues

2009

A convenient synthesis of the pyrano[2,3-e]isoindol-2-one ring system, an heteroanalogue of angelicin, is reported. Our synthetic approach consists of the annelation of the pyran ring on the isoindole moiety using 5-dialkylamino- or 5-hydroxymethylene intermediates as building blocks. The photoantiproliferative activity of the new derivatives was studied. Some of them bearing the benzyl group at the 8 position were active with IC(50) in the micromolar range. Cell cytotoxicity involves apoptosis, alteration of cell cycle profile and membrane photodamage.

Maleic diamide polymerizable surfactants. Applications in emulsion polymerization

2003

Abstract A series of new polymerizable non-ionic and ionic surfactants (surfmers) with amides groups on both sides of the C=C double bonds have been prepared upon reaction of maleic isoimide carrying a long alkyl chain (or a benzyl group) with a hydrophilic amine derivative. Their critical micellar concentration (CMC) was measured with a surface tensiometer. They have been engaged in batch emulsion polymerization of styrene, and semi-batch seeded copolymerization of styrene and butyl acrylate, giving stable latexes during the polymerization process, and upon extraction with ethanol, showing a high rate of incorporation at the particle surface. However these surfmers do not confer good steri…

Synthesis and Structure-Affinity Relationships of Spirocyclic Benzopyrans with Exocyclic Amino Moiety

2019

σ1 and/or σ2 receptors play a crucial role in pathological conditions such as pain, neurodegenerative disorders, and cancer. A set of spirocyclic cyclohexanes with diverse O-heterocycles and amino moieties (general structure III) was prepared and pharmacologically evaluated. In structure-activity relationships studies, the σ1 receptor affinity and σ1:σ2 selectivity were correlated with the stereochemistry, the kind and substitution pattern of the O-heterocycle, and the substituents at the exocyclic amino moiety. cis-configured 2-benzopyran cis-11b bearing a methoxy group and a tertiary cyclohexylmethylamino moiety showed the highest σ1 affinity ( Ki = 1.9 nM) of this series of compounds. In…

PHOSPHORORGANISCHE VERBINDUNGEN 105.1Synthese chiraler und achiraler ditertiärer 1-Phosphino-2-Aminoethan-Derivate ([dbnd]P [sbnd]CH2[sbnd]CHR[sbnd]N…

1983

Abstract Primary amines with an optical active ligand add to vinyl- and propenylphosphonium salts according the reaction schemes (5) and (6), forming compounds of the type E and F. F contains a new asymmetric center in the bridge giving rise to the formation of a mixture of diastereomers, which can be resolved. Phosphonium salts of type E and F with a benzyl group on the phosphonium center are cleaved reductively by alkali amalgams (Li/Hg; Na/Hg; K/Hg) forming tertiary phosphines with an aminogroup in the β-position. The reductive cleavage with alkali amalgams is superior to the cathodic cleavage. Application: The synthesis of Ni(O)- and Pd(O)-complexes of type J fails. Bis-phosphine comple…

1,3-Oxazin-2-ones vs tetrahydrofurans by iodocyclisation of 2-alkoxycarbonylamino-3-alken-1-ols

2000

Abstract Iodocyclisation of primary homoallylic alcohols 2a – d , containing either a 2- t -butoxy- or a benzyloxycarbonylamino group, was studied, in order to establish the nucleophilic group involved in cyclofunctionalisation. In fact, the N - t -Boc derivative 2a gave the oxazinone 3 , exclusively, whereas starting from the N -Cbz derivative 2b a diastereomeric mixture of substituted tetrahydrofurans 4 and 5 resulted in ratios depending upon the reaction conditions. These results were rationalised by means of computational methods. On the contrary, migration of both the t -butyl or benzyl group to the hydroxy group was observed when both 2c and 2d underwent cyclisation to give the corres…

2015

The heterotetracene skeleton of the title molecule, C23H14Br2N2OS, is defined by linear annulation of four six-membered rings, including two N heteroatoms. This moiety is nearly planar (r.m.s. deviation = 0.055 Å), with a slight twist of 4.1 (2)° between the two halves of the aromatic system. The dihedral angle between the least-squares plane of the skeleton and the benzyl group is 24.5 (3)°; the C—S—C angle involving the benzylsulfanyl group is 99.2 (4)°. In the crystal, molecules are π-stacked in an antiparallel fashion along [110], with a distance between the aromatic planes of 3.47 (2) Å. Intermolecular N—H...O hydrogen bonds form chains extending parallel to [001] and bridge the antipa…