Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

• Layal Hariss,
• Kamal Bou Hadir,
• Mirvat El-Masri,
• Thierry Roisnel,
• René Grée and
• Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

• coupling reactions as well as nucleophilic substitutions have been performed successfully in order to increase the molecular diversity. Keywords: aerobic oxidative coupling; imidazo[1,2-a]-N-heterocycles; gem-difluoroalkyl derivatives; propargylic fluorides; Introduction Nitrogen-containing heterocyclic

• with gem-fluorinated side chains starting from easily accessible propargylic fluorides. Although the yields are only moderate to fair, this short (1–2 steps) method offers significant flexibility to prepare focused libraries of molecules with this core structure. Such new fluorine-containing

• heteroaromatic frameworks would be of much interest for biological studies in different areas of life sciences. Experimental Representative procedure for the synthesis of imidazopyridine 7a The syntheses of propargylic fluorides 5 and enones 6 were performed in a similar way as described before [26]. Synthesis

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

• Santos Fustero,
• Paula Bello,
• Javier Miró,
• María Sánchez-Roselló,
• Günter Haufe and
• Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

• CEYM reaction, ethylene does not incorporate into the product but intercepts the secondary metathesis pathways avoiding the formation of secondary products during the process [17][18]. Among organic fluorine compounds, propargylic fluorides constitute a relevant class of fluorinated building blocks

• . The transformational diversity of the alkynyl group converts them into versatile synthetic intermediates. Additionally, propargylic fluorides are prevalent motifs in life sciences, such as medicinal chemistry or crop protection. In this context, the preparation of monofluorinated propargylic compounds

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

• Assaad Nasr El Dine,
• Ali Khalaf,
• Danielle Grée,
• Olivier Tasseau,
• Fares Fares,
• Nada Jaber,
• Philippe Lesot,
• Ali Hachem and
• René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

• to investigate the preparation and uses of new propargylic fluorides [12][13][14], which have been employed in the synthesis of fluorinated analogues of lipids [15][16] and in carbocyclic systems [17][18]. They have also been used for the preparation of several 5 and 6-membered heterocycles [19][20