Synthesis of 5-arylmethylidene-3-(arylmethylideneamino)thiazolidine-2,4-diones via triazine ring cleavage of tetrahydroimidazothiazolotriazinediones and their reactions with azomethine ylides

Izmest’ev, Alexei N.; Газиева, Галина А.; Kolotyrkina, N. G.; Даева, Е. Д.; Кравченко, Ангелина Н.

doi:10.1007/s10593-020-02851-w

Cited by 14 publications

(3 citation statements)

References 16 publications

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“…Finally, we have studied 1,3‐dipolar cycloaddition reaction of some oxindolylidene derivatives 5 and 6 with azomethine ylides generated in situ from paraformaldehyde and N‐alkyl amino acids using a procedure similar to one described earlier [3,10] . 1,3‐Dipole was thermally generated by a reaction between paraformaldehyde and an amino acid in boiling solvent via formation of an iminium intermediate which underwent cyclization with subsequent loss of CO 2 [10,11] .…”

Section: Resultsmentioning

confidence: 99%

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5‐Indolylidene‐2‐iminothiazolidin‐4‐ones – Convenient Starting Compounds for Stereoselective Synthesis of Novel Dispirooxindole Derivatives

et al. 2022

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A convenient method for the synthesis of novel dispirooxindoles containing 2‐iminothiazolidin‐4‐one moiety has been proposed. The method relies on a 1,3‐dipolar cycloaddition of azomethine ylides generated in situ from paraformaldehyde and N‐alkyl amino acids including chiral ones to 5‐indolylidene‐2‐iminothiazolidin‐4‐ones. The method is suitable for preparing enantiomerically pure derivatives.

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Section: Resultsmentioning

confidence: 99%

“… [2a,b] Thiazolidinones containing spirolinked pyrrolidinoxindole fragments were also investigated for different types of activity. These compounds turned out to exhibit a weak antiproliferative effect, [2c,3] however, they possessed attractive anti‐diabetic properties to male Wistar rats (see Figure 1). [4] …”

Section: Introductionmentioning

confidence: 99%

5‐Indolylidene‐2‐iminothiazolidin‐4‐ones – Convenient Starting Compounds for Stereoselective Synthesis of Novel Dispirooxindole Derivatives

et al. 2022

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“…A convenient and effective method for the synthesis of spirooxindoles is the [3+2] cycloaddition reaction of azomethine ylides to unsaturated compounds [14][15][16][17][18][19][20][21][22][23][24][25][26][27]. Such reactions often proceed with high diastereoselectivity and allow to obtain products with a certain relative configuration, while other isomers remain unavailable.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of Dispiro[Imidazothiazolotriazine-Pyrrolidin-Oxindoles] and Their Isomerization Pathways in Basic Medium

Izmest′ev,

Vinogradov,

Kravchenko

et al. 2023

IJMS

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Highly diastereoselective methods for the synthesis of two series of regioisomeric polynuclear dispyroheterocyclic compounds with five or six chiral centers, comprising moieties of pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine of linear structure or imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine of angular structure, have been developed on the basis of a [3+2] cycloaddition of azomethine ylides to functionalized imidazothiazolotriazines. Depending on the structure of the ethylenic component, cycloaddition proceeds as an anti-exo process for linear derivatives, while cycloaddition to angular ones resulted in a syn-endo diastereomer. Novel pathways of isomerization for the synthesized anti-exo products upon treatment with sodium alkoxides have been found, which resulted in two more series of diastereomeric dispiro[imidazothiazolotriazine-pyrrolidin-oxindoles] inaccessible with the direct cycloaddition reaction. For the first series, the inversion of the configuration of one stereocenter, i.e., C-4′ atom of the pyrrolidine cycle, (epimerization) was established. For the second one, configuration of the obtained diastereomer formally corresponded to the syn-endo approach of the azomethine ylide in the case of cycloaddition to the ethylenic component.

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Regioselective Synthesis of Imidazo[4,5‐e][1,3]Thiazino[3,2‐b][1,2,4]Triazines as New Heterocyclic System Derivatives

Izmest'ev,

Baranov,

Kolotyrkina

et al. 2024

Journal of Heterocyclic Chem

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A series of new 4a,7a‐diarylperhydroimidazo[4,5‐e][1,2,4]triazine‐3‐thiones were synthesized from 4,5‐diaryl‐4,5‐dihydroxyimidazolidin‐2‐ones and thiosemicarbazide in high yields, and their interaction with ethyl phenylpropiolate was studied. An effective method for the regioselective synthesis of imidazo[4,5‐e][1,3]thiazino[3,2‐b][1,2,4]triazines as new heterocycic system derivatives was proposed based on the reaction of aforementioned imidazotriazinethiones with ethyl phenylpropiolate in the presence of MeONa in methanol. The reaction is initiated by a Michael‐type addition of the imidazotriazinethiones to the triple bond of ethyl phenylpropiolate followed by intramolecular cyclization.

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Synthesis of 5-arylmethylidene-3-(arylmethylideneamino)thiazolidine-2,4-diones via triazine ring cleavage of tetrahydroimidazothiazolotriazinediones and their reactions with azomethine ylides

Cited by 14 publications

References 16 publications

5‐Indolylidene‐2‐iminothiazolidin‐4‐ones – Convenient Starting Compounds for Stereoselective Synthesis of Novel Dispirooxindole Derivatives

5‐Indolylidene‐2‐iminothiazolidin‐4‐ones – Convenient Starting Compounds for Stereoselective Synthesis of Novel Dispirooxindole Derivatives

Diastereoselective Synthesis of Dispiro[Imidazothiazolotriazine-Pyrrolidin-Oxindoles] and Their Isomerization Pathways in Basic Medium

Regioselective Synthesis of Imidazo[4,5‐e][1,3]Thiazino[3,2‐b][1,2,4]Triazines as New Heterocyclic System Derivatives

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