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

S. V. Borisova; Борисова Светлана Васильевна; A. A. Meshcheryakova; Мещерякова Анна Аркадьевна; V. V. Sorokin; Сорокин Виталий Викторович

doi:10.31857/S0044460X24040038

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

Authors: Borisova S.V.¹, Meshcheryakova A.A.², Sorokin V.V.²
Affiliations:
1. Saratov State Medical University named after V. I. Razumovsky
2. Saratov State University named after N. G. Chernyshevsky
Issue: Vol 94, No 4 (2024)
Pages: 489-502
Section: Articles
URL: https://journals.rcsi.science/0044-460X/article/view/262779
DOI: https://doi.org/10.31857/S0044460X24040038
EDN: https://elibrary.ru/EBMKQF
ID: 262779

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Abstract

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.

Keywords

spirooxoindoles, 1,3-dipolar cycloaddition, azomethine ylides, idemalononitriles, retro-1,3-dipolar cycloaddition

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