No abstract

International audienc

1,3-dipolar cycloaddition of (E)-arylidene-(2H)-indanones 1 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-NO2C6H4) and (E)-2-arylidene-(2H)-tetralones 2 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-NO2C6H4) to N-metalated azomethine ylides 3 generated from methyl N-arylideneglycinate in the presence of silver acetate produces in good yields novel methyl 1-oxo-2',4'-diaryl-1,3-dihydrospiro[indene-2,3'-pyrrolidine]-5'-carboxylates 4 and methyl 1-oxo-2',4'-diaryl-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-5'carboxylates 5. The cycloaddition proceeds in regio-and stereoselective manner (100%) at room temperature to afford respectively the syn-endo cycloadducts 4 and 5 via metallo-azomethine ylides. The regio-and stereochemistry of the spiranic adducts have been established on the basis of spectroscopic data and elemental analysis, corroborated by single-crystal X-ray crystallographic analysis of the heterocycles 4ci, 4bg and 5bi. The endo-pyrrolidines 4 were brominated by N-bromosuccinimide to give finally the dehydrobrominated 3, 4dihydro-2H-pyrrole derivatives 6. The spiro-adducts 4 and their corresponding oxidation products 6 are fluorescent in solution.

VI)] are synthesized in good yields by three-component 1,3-dipolar cycloaddition reactions. The procedure features high regio-and stereoselectivity and high tolerance towards the electronic properties of the substituents at the aryl group in compounds (III). The products are screened for their antimycobacterial and cytotoxic activities. Reaction mechanism and structure-activity relationship are discussed. -(MHIRI, C.; BOUDRIGA, S.; ASKRI*, M.; KNORR, M.; SRIRAM, D.; YOGEESWARI, P.; NANA, F.; GOLZ, C.; STROHMANN, C.; Bioorg. Med. Chem. Lett. 25 (2015) 19, 4308-4313, http://dx.