Bicyclic -dihalocyclopropylamide derivatives as precursors of nitrogen-containing fused polycyclic systems.

Examples of carbon-carbon bond-forming cyclisation reactions, involving allyl cations generated by the thermal ring-opening of halocyclopropanes, have been scarcely reported. In this contribution, we are describing the results of a study conducted with -dihalocyclopropylamide substrates, designed as precursors of cyclic iminium intermediates that were aimed at participating in intramolecular reactions with electron-rich aromatic groups. Competitive side-reactions were identified, and access to the desired polycyclic products was carefully evaluated.

Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells.

The Heck cross-coupling reaction is a well-established chemical tool for the synthesis of unsaturated compounds by formation of a new C-C bond. In this study, 1,3-diarylpropene derivatives, designed as structural analogues of stilbenoids and dihydrostilbenoids, were synthesised by the palladium-catalysed reactions of 2-amidoiodobenzene derivatives with either estragole or eugenol. The products were obtained with high (E) stereoselectivity but as two regioisomers.

Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives.

A series of 6,6-dihalo-2-azabicyclo[3.1.0]hexane and 7,7-dihalo-2-azabicyclo[4.

Access to new endoperoxide derivatives by electrochemical oxidation of substituted 3-azabicyclo[4.1.0]hept-4-enes.

A series of substituted 3-azabicyclo[4.1.0]hept-4-ene derivatives were prepared and analysed by cyclic voltammetry.

Synthesis of polycyclic aminocyclobutane systems by the rearrangement of N-(ortho-vinylphenyl) 2-azabicyclo[3.1.0]hexane derivatives.

The acid-catalysed thermal rearrangements of a family of N-aryl 2-azabicyclo[3.1.0]hexanes is described.

Kulinkovich-type reactions of thioamides: similar to those of carboxylic amides?

The behaviour of thioamides under Kulinkovich-type conditions is compared with the known reactivity of carboxylic amides. Dramatic differences are disclosed.

Aminocyclopropanes as precursors of endoperoxides with antimalarial activity.

This contribution describes the synthesis of several novel bicyclic α-amino endoperoxides, including CF(3)-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovich-de Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented.

Studies on the intramolecular Kulinkovich-de Meijere reaction of disubstituted alkenes bearing carboxylic amide groups.

1,2-Disubstituted olefins bearing an acetamide group were found to undergo intramolecular Kulinkovich-de Meijere cyclopropanation in moderate yield but almost complete diastereoselectivity.