A novel synthesis of tricyclic-fused hydrindene–azetidinone compounds by sequential Mn(III)-promoted 4- exo-trig cyclization/radical aromatic substitution

The 2-acyl- N-(2,2-diphenyl-1-ethenyl)- N-alkylacetamides reacted with excess Mn(III) affording tricyclic fused hydrindene-azetidinones in good yields, through a 4- exo-trig radical cyclization process, and further ring closure of the azetidinone via radical aromatic substitution.

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Bibliographic Details
Published in:Tetrahedron letters 2000-04, Vol.41 (17), p.3261-3264
Main Authors: Cerreti, Alessandra, D'Annibale, Andrea, Trogolo, Corrado, Umani, Floriana
Format: Article
Language:English
Subjects:
azetidinones
cyclization
manganese and compounds
polycyclic heterocyclic compounds
radicals and radical reaction
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Summary:The 2-acyl- N-(2,2-diphenyl-1-ethenyl)- N-alkylacetamides reacted with excess Mn(III) affording tricyclic fused hydrindene-azetidinones in good yields, through a 4- exo-trig radical cyclization process, and further ring closure of the azetidinone via radical aromatic substitution.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00364-6