Synthesis of highly substituted spiropyrrolidines via 1, 3-dipolar cycloaddition reaction of N-metalated azomethine ylides. A new access to spiropyrroline derivatives - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Mediterranean Journal of Chemistry Année : 2015

Synthesis of highly substituted spiropyrrolidines via 1, 3-dipolar cycloaddition reaction of N-metalated azomethine ylides. A new access to spiropyrroline derivatives

Résumé

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, 4-dihydro-2H-pyrrole derivatives 6. The spiro-adducts 4 and their corresponding oxidation products 6 are fluorescent in solution.

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Chimie
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Dates et versions

hal-01277418 , version 1 (22-02-2016)

Identifiants

  • HAL Id : hal-01277418 , version 1

Citer

C. Mhiri, R. Fadwa, Boudriga S., M. Askri, K. Ciamala, et al.. Synthesis of highly substituted spiropyrrolidines via 1, 3-dipolar cycloaddition reaction of N-metalated azomethine ylides. A new access to spiropyrroline derivatives. Mediterranean Journal of Chemistry, 2015, 4 (1), pp.30-50. ⟨hal-01277418⟩
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