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

ABSTRACT: The regioselective three-component condensation of azomethine ylides derived from isatins and ?-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.

SUBMITTER: Pavlovskaya TL

PROVIDER: S-EPMC3896290 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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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 TL Yaremenko Fedor G FG Lipson Victoria V VV Shishkina Svetlana V SV Shishkin Oleg V OV Musatov Vladimir I VI Karpenko Alexander S AS

Beilstein journal of organic chemistry 20140109

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. ...[more]

PMID: 24454564

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