Interconversions of 1,3-dipolar cycloaddition products of azomethine ylides and ylidenemalononitriles

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New substituted spiropyrrole(zi)dynes were synthesized by the 1,3-dipolar cycloaddition reaction of ylidenemalononitriles and azomethine ylides generated in situ by condensation of isatin and α-amino acids (sarcosine, proline). The products′s features of the regio- and diastereochemical structure were elucidated depending on the nature of the amino acid and the reaction conditions. Based on data from the analysis of the spectra of cycloaddition products obtained under various conditions, as well as some additional experiments, a probable scheme for the formation of products was proposed, including retro-1,3-dipolar cycloaddition and the retro-Mannich reaction. Methods for the selective synthesis of isomeric spiropyrrolizidines were developed.

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S. Borisova

Saratov State Medical University named after V. I. Razumovsky

编辑信件的主要联系方式.
Email: chuvaikinasv@gmail.com
ORCID iD: 0000-0001-8025-1296
俄罗斯联邦, Saratov, 410012

A. Meshcheryakova

Saratov State University named after N. G. Chernyshevsky

Email: chuvaikinasv@gmail.com
ORCID iD: 0000-0002-8039-1106
俄罗斯联邦, Saratov, 410012

V. Sorokin

Saratov State University named after N. G. Chernyshevsky

Email: chuvaikinasv@gmail.com
ORCID iD: 0000-0002-5861-3307
俄罗斯联邦, Saratov, 410012

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