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. 2014 Jan 9:10:117-26.
doi: 10.3762/bjoc.10.8.

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

Tatyana L Pavlovskaya  1 , Fedor G Yaremenko  2 , Victoria V Lipson  3 , Svetlana V Shishkina  1 , Oleg V Shishkin  4 , Vladimir I Musatov  1 , Alexander S Karpenko  5
Affiliations

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

Tatyana L Pavlovskaya et al. Beilstein J Org Chem. .

Abstract

The regioselective three-component condensation of azomethine ylides derived from isatins and α-amino acids with acrylamides or 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 cyclative rearrangement with formation of dihydropyrrolizinyl indolones.

Keywords: acrylamides; aroylacrylic acids; azomethine ylide; cyclative rearrangement; cycloaddition; multicomponent; spirooxindoles.

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Figures

Figure 1
Figure 1
The NOE correlations of the signals in 1H NMR spectra of compounds 4b–4d.
Figure 2
Figure 2
Molecular structure of spirooxindole 4a according to X-ray diffraction data.
Figure 3
Figure 3
The NOE correlations of the signals in 1H NMR spectrum of compound 6c.
Figure 4
Figure 4
Molecular structure of spirooxindole 6a observed in crystal phase as solvate with methanol according to X-ray diffraction data.
Scheme 1
Scheme 1
The mechanism of the regioselective synthesis of compounds 4 and 6.
Figure 5
Figure 5
Conformations of acrylamide and benzoylacrylic acid.
Figure 6
Figure 6
The Fukui function indices of acrylamide, azomethine ylide and benzoylacrylic acid.
Scheme 2
Scheme 2
The synthesis of compounds 7a–7c.
Figure 7
Figure 7
The selected COSY, NOESY and HMBC correlations of the signals in the 1H and 13C NMR spectra of compound 7a.
Scheme 3
Scheme 3
Tentative reaction mechanism for the decarboxylative cyclative rearrangement of the initial three-component product.
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