A strategic approach for synthesis of benzimidazo[2,1-b]thiazolidinone appended dispirooxindole hybrids via [3 + 2] cycloaddition using fluoro-ethanol as solvent

Bhardwaj, Diksha; Singh, Ruby

doi:10.1016/j.tetlet.2021.153491

Cited by 3 publications

(3 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2). Herein, as a part of our endeavour to create a novel bioactive heterocyclic hybrids [37][38][39][40] we report the synthesis of benzo [4,5]thiazolo[2,3-c][1,2,4]triazole derivatives and thiazolidinone-appended benzo [4,5]…”

Section: Introductionmentioning

confidence: 99%

“…2). Herein, as a part of our endeavour to create a novel bioactive heterocyclic hybrids 37–40 we report the synthesis of benzo[4,5]thiazolo[2,3- c ][1,2,4]triazole derivatives and thiazolidinone-appended benzo[4,5]thiazolo[2,3- c ][1,2,4]triazole derivatives by employing cost-effective starting materials in a one-pot process and further evaluated them for their antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Green design and synthesis of some novel thiazolidinone appended benzothiazole–triazole hybrids as antimicrobial agents

Dwivedi,

Bhardwaj,

Choudhary

2024

RSC Adv.

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Green design and synthesis of some novel thiazolidinone appended benzothiazole–triazole hybrids as antimicrobial agents

Dwivedi,

Bhardwaj,

Choudhary

2024

RSC Adv.

Self Cite

View full text Add to dashboard Cite

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

Synthesis, Structure and Stereochemistry of Dispirocompounds Based on Imidazothiazolotriazine and Pyrrolidineoxindole

Izmest’ev

Карноухова

Larin

et al. 2022

IJMS

View full text Add to dashboard Cite

Methods for the synthesis of two types of isomeric dispirocompounds based on imidazothiazolotriazine and pyrrolidineoxindole, differing in the structure of imidazothiazolotriazine fragment, namely, linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidine- 4′,3″-indolines] and angular dispiro[imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-7,3′-pyrrolidine-4′,3″-indolines] were proposed. The first method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from paraformaldehyde and N-alkylglycine derivatives to the corresponding oxindolylidene derivatives of imidazothiazolotriazine. The cycloaddition leads to a mixture of two diastereomers resulted from anti- and syn-approaches of azomethine ylide in approximately a 1:1 ratio, which were separated by column chromatography. Another method consists in rearrangement of linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidine-4′,3″-indolines] into hitherto unavailable angular dispiro[imidazo[4,5-e]thiazolo[2,3-c]-[1,2,4]triazine-7,3′-pyrrolidine-4′,3″-indolines] upon treatment with KOH. It was found that the anti-diastereomer of linear type underwent rearrangement into the isomeric angular syn-diastereomer, while the rearrangement of the linear syn-diastereomer gave the angular anti-diastereomer.

show abstract

A strategic approach for synthesis of benzimidazo[2,1-b]thiazolidinone appended dispirooxindole hybrids via [3 + 2] cycloaddition using fluoro-ethanol as solvent

Cited by 3 publications

References 51 publications

Green design and synthesis of some novel thiazolidinone appended benzothiazole–triazole hybrids as antimicrobial agents

Green design and synthesis of some novel thiazolidinone appended benzothiazole–triazole hybrids as antimicrobial agents

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

Synthesis, Structure and Stereochemistry of Dispirocompounds Based on Imidazothiazolotriazine and Pyrrolidineoxindole

Contact Info

Product

Resources

About