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

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�...

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Autores principales: Pavlovskaya, Tatyana L, Yaremenko, Fedor G, Lipson, Victoria V, Shishkina, Svetlana V, Shishkin, Oleg V, Musatov, Vladimir I, Karpenko, Alexander S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3896290/
https://www.ncbi.nlm.nih.gov/pubmed/24454564
http://dx.doi.org/10.3762/bjoc.10.8
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author Pavlovskaya, Tatyana L
Yaremenko, Fedor G
Lipson, Victoria V
Shishkina, Svetlana V
Shishkin, Oleg V
Musatov, Vladimir I
Karpenko, Alexander S
author_facet Pavlovskaya, Tatyana L
Yaremenko, Fedor G
Lipson, Victoria V
Shishkina, Svetlana V
Shishkin, Oleg V
Musatov, Vladimir I
Karpenko, Alexander S
author_sort Pavlovskaya, Tatyana L
collection PubMed
description 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.
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spelling pubmed-38962902014-01-21 The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids Pavlovskaya, Tatyana L Yaremenko, Fedor G Lipson, Victoria V Shishkina, Svetlana V Shishkin, Oleg V Musatov, Vladimir I Karpenko, Alexander S Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2014-01-09 /pmc/articles/PMC3896290/ /pubmed/24454564 http://dx.doi.org/10.3762/bjoc.10.8 Text en Copyright © 2014, Pavlovskaya et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Pavlovskaya, Tatyana L
Yaremenko, Fedor G
Lipson, Victoria V
Shishkina, Svetlana V
Shishkin, Oleg V
Musatov, Vladimir I
Karpenko, Alexander S
The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids
title The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids
title_full The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids
title_fullStr The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids
title_full_unstemmed The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids
title_short The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids
title_sort regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3896290/
https://www.ncbi.nlm.nih.gov/pubmed/24454564
http://dx.doi.org/10.3762/bjoc.10.8
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