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Cycloaddition of C,C‐Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5‐Spirocyclopropane‐isoxazolidines
Author(s) -
Tran Tung Q.,
Diev Vyacheslav V.,
Starova Galina L.,
Gurzhiy Vladislav V.,
Molchanov Alexander P.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200039
Subject(s) - chemistry , cycloaddition , aryl , methylenecyclopropane , ring (chemistry) , stereochemistry , medicinal chemistry , acceptor , catalysis , organic chemistry , alkyl , physics , condensed matter physics
A new reaction cascade to give tricyclic cores of 2,4‐dihydro‐1 H ‐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‐1 H ‐azeto[1,2‐ a ]quinolines 4 or pyrrolo[1,2‐ a ]quinolines 6 .