Beilstein J. Org. Chem.2014,10, 117–126, doi:10.3762/bjoc.10.8
aroylacrylicacids as dipolarophiles has been realized through a one-pot 1,3-dipolar cycloaddition protocol. Decarboxylation of 2'-aroyl-2-oxo-1,1',2,2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizine]-1'-carboxylic acids is accompanied by cyclative rearrangement with formation of dihydropyrrolizinyl
indolones.
Keywords: acrylamides; aroylacrylicacids; azomethine ylide; cyclative rearrangement; cycloaddition; multicomponent; spirooxindoles; Introduction
The design of new spirocyclic compounds is intriguing due to their unique non-planar structure and great potential for binding to biomolecules due to
inhibitors there are compounds containing a pyrrolidine-2-one as a part of the spirocyclic system [34].
In the present work we report the synthesis of spirooxindolo pyrrolidines and pyrrolizidines by utilizing a 1,3-dipolar cycloaddition of hitherto uninvestigated acrylamides and aroylacrylicacids with
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Graphical Abstract
Figure 1:
The NOE correlations of the signals in 1H NMR spectra of compounds 4b–4d.