Comparative study of chemically immobilized and conventional homogeneous ionic liquids as phase-transfer catalysts for the N-alkylation of heterocyclic compounds

Dogra, Shallu; Sharma, M. L.; Singh, J. B.

doi:10.1016/j.crci.2015.02.004

Cited by 5 publications

(1 citation statement)

References 43 publications

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“…As shown in Fig. 5a , the IR stretching vibration absorbance of the carbonyl group at 1735 cm −1 assigning to DS decreased gradually as the reaction proceeded 30 , meanwhile two peaks appeared at 1709 and 1680 cm −1 , which became more and more intense 31 , ascribing to the IR stretching vibration absorbance of carbonyl groups in 3f and 4f 32 , respectively. In Fig.…”

Section: Resultsmentioning

confidence: 86%

Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids

Wu,

Wang,

Zhao

et al. 2024

Nat Commun

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The chemical transformation of waste polymers into value-added chemicals is of significance for circular economy and sustainable development. Herein, we report upcycling poly(succinates) (PSS) with amines into N-substituted succinimides over succinimide anion-based ionic liquids (ILs, e.g, 1,8-diazabicyclo[5.4.0]undec-7-ene succinimide, [HDBU][Suc]). Assisted with H2O, [HDBU][Suc]) showed the best performance, which could achieve complete transformation of a series of PSS into succinimide derivatives and corresponding diols under mild and metal-free conditions. Mechanism investigation indicates that the cation-anion confined hydrogen-bonding interactions among IL, H2O, ester group, and amino/amide groups, strengthens nucleophilicity of the N atoms in amino/amide groups, and improves electrophilicity of carbonyl C atom in ester group. The attack of the amino/amide N atom on carbonyl C of ester group results in cleavage of carbonyl C-O bond in polyester and formation of amide group. This strategy is also effective for aminolysis of poly(trimethylene glutarate) to glutarimides, and poly(1,4-butylene adipate) to caprolactone diimides.

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Section: Resultsmentioning

confidence: 86%

Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids

Wu,

Wang,

Zhao

et al. 2024

Nat Commun

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Synthesis and kinetic study of N-(1-methyl-3-phenyl-propane)-phthalimide (NP) by phase-transfer catalysis assisted by ultrasound irradiation

Brahmayya

Wang

2016

Res Chem Intermed

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Improved Synthesis of the Antitubercular Agent SQ109

Stampolaki

Kolocouris²

2021

SynOpen

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We presented here an improved procedure for the preparation of the promising anti-tubercular drug SQ109 (10) which is currently in phase Ib/III of clinical trials against Mycobacterium tuberculosis. We investigated and tested the literature synthetic procedure that enables the development of structure-activity relationships and reported the observed inconsistencies as well as presented improvements or novelties for the more efficient preparation of SQ109 (10). Most significantly we applied a novel reduction step of the aminoamide precursor using Me3SiCl/LiAlH4 under mild conditions in the synthesis of SQ109 (10). These findings are important for research groups investigating the efficacy of this drug and analogues in academia and industry.

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Comparative study of chemically immobilized and conventional homogeneous ionic liquids as phase-transfer catalysts for the N-alkylation of heterocyclic compounds

Cited by 5 publications

References 43 publications

Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids

Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids

Synthesis and kinetic study of N-(1-methyl-3-phenyl-propane)-phthalimide (NP) by phase-transfer catalysis assisted by ultrasound irradiation

Improved Synthesis of the Antitubercular Agent SQ109

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