Cycloaddition of C,C‐Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5‐Spirocyclopropane‐isoxazolidines
Cycloaddition of C,C‐Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5‐Spirocyclopropane‐isoxazolidines
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DOI：
10.1002/ejoc.201200039
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发表时间：
2012-04
影响因子：
2.8
通讯作者：
T. Tran;V. V. Diev-V.;G. Starova;V. Gurzhiy;A. Molchanov
中科院分区：
文献类型：
--
作者：
T. Tran;V. V. Diev-V.;G. Starova;V. Gurzhiy;A. Molchanov
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 Brandi–Guarna 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.
