SummaryStarting from easily accessible gem-difluoropropargylic derivatives, a DBU-mediated isomerisation affords enones in fair yields with a gem-difluoroalkyl chain. These derivatives were used to prepare pyrazolines and pyrrolines with the desired gem-difluoroalkyl side chain by cyclocondensations in good yields and with excellent stereoselectivity. A one-pot process was also successfully developed for these sequential reactions. By carrying out various types of Pd-catalyzed coupling reactions for compounds with a p-bromophenyl substituent a route to focused chemical libraries was demonstrated.
International audienceThe Kinugasa reaction applied to alkynes bearing a nucleofuge in propargylic position affords directly, and in fair yields, α-methylene- or α-alkylidene- β-lactam
As part of our studies focused on the design and synthesis of biologically active molecules, polyheterocyclic compound 3 was prepared in one step from commercially available 2-aminothiophenol 1 and 2,5-dihydro-2,5-dimethoxyfuran 2. Derivative 3 underwent a further isomerization to compound 4 in a reaction promoted by traces of HCl in chloroform.
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