Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 10, Pages 2054-2061Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200039
Keywords
Cycloaddition; Rearrangement; Nitrones; Small ring systems; Methylenecyclopropanes
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Funding
- Ministry of Education and Training of Vietnam
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A new reaction cascade to give tricyclic cores of 2,4-dihydro-1H-azeto[1,2-a]quinolines (benzocarbacephems) and pyrrolo[1,2-a]quinolines starting from acyclic N-aryl ketonitrones and acceptor ring substituted methylenecyclopropanes has been reported. This reaction includes 1,3-dipolar cycloaddition of N-aryl-C,C-diaryl or N-aryl-C,C-bis(methoxycarbonyl) nitrones 1 to the double bond of dimethyl methylenecyclopropane-1,2-dicarboxylate 2 or benzylidenecyclopropane-1,1-dicarboxylate 3, followed by BrandiGuarna rearrangement of the initially formed 5-spirocyclopropane-isoxazolidine cycloadducts to give 2,4-dihydro-1H-azeto[1,2-a]quinolines 4 or pyrrolo[1,2-a]quinolines 6.
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