Beilstein J. Org. Chem.2014,10, 117–126, doi:10.3762/bjoc.10.8
aroylacrylic acids 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 cyclativerearrangement with formation of dihydropyrrolizinyl
indolones.
Keywords: acrylamides; aroylacrylic acids; azomethine ylide; cyclativerearrangement; 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
of compound 7a.
The mechanism of the regioselective synthesis of compounds 4 and 6.
The synthesis of compounds 7a–7c.
Tentative reaction mechanism for the decarboxylative cyclativerearrangement of the initial three-component product.
Three-component synthesis of spirooxindoles 4a–4g.
Synthesis of
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Graphical Abstract
Figure 1:
The NOE correlations of the signals in 1H NMR spectra of compounds 4b–4d.