Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives

Valeru, Anil; Luo, Zhibin; Khan, Imran; Liu, Bin; Sngepu, Bhavanarushi; Godumagadda, Narender Reddy; Xu, Yin; Xie, Jimin

doi:10.1080/00397911.2018.1490769

Cited by 9 publications

(4 citation statements)

References 25 publications

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“…In conclusion, a one-pot, multi-component, ecofriendly, simple but efficient methodology for the synthesis of 3,4-dihydropyrimidin-2-(1H)-one and its thione derivatives has been developed by employing [EMIM] AlCl 4 -ionic liquid in ethanol under grinding conditions. The concept of mechanochemistry using ionic liquid as a [37] 4t 12 90 168-170 [38] 4u 16 85 210-212 [39] (Continues) catalyst in the eco-friendly solvent is demonstrated for the Biginelli reaction. The reaction between various aliphatic/aromatic/heterocyclic aldehydes, methyl/ethyl/trifluoromethyl acetoacetate, and urea/thiourea was carried out successfully under the optimized reaction condition (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

[EMIM]AlCl₄‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives

Popatkar

Sasane

Meshram

2023

Journal of Heterocyclic Chem

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[EMIM]AlCl4 (1‐ethyl‐3‐methylimidazolium tetrachloroaluminate) ionic liquid catalyzed mechanochemically assisted methodology for the Biginelli reaction has been developed successfully. One‐pot, multicomponent reaction between ethyl/methyl acetoacetate, urea/thiourea, and various aromatic/aliphatic and heterocyclic aldehydes in presence of catalytic amount of [EMIM]AlCl4 under grinding conditions in ethanol affords 3,4‐dihydropyrimidin‐2‐(1H)‐one and its thione derivatives. Short reaction time, inclusion of eco‐friendly solvent, moderate to high yield of the product, and operational simplicity are some of the noteworthy features of this protocol. In consequence, the described procedure finds an alternative way to existing methods for the synthesis of the titled compounds.

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Section: Resultsmentioning

confidence: 99%

[EMIM]AlCl₄‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives

Popatkar

Sasane

Meshram

2023

Journal of Heterocyclic Chem

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“…Ethyl 2-oxo-4-phenyl-6-trifluoromethyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate ( 4j ) [ 35 ]. Yellow solid (0.580 g).…”

Section: Methodsmentioning

confidence: 99%

Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones via a Three-Component Biginelli Reaction

et al. 2021

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Multicomponent reactions are considered to be of increasing importance as time progresses due to the economic and environmental advantages such strategies entail. The three-component Biginelli reaction involves the combination of an aldehyde, a β-ketoester and urea to produce 3,4-dihydropyrimidin-2(1H)-ones, also known as DHPMs. The synthesis of these products is highly important due to their myriad of medicinal properties, amongst them acting as calcium channel blockers and antihypertensive and anti-inflammatory agents. In this study, silicotungstic acid supported on Ambelyst-15 was used as a heterogeneous catalyst for the Biginelli reaction under solventless conditions. Electron-poor aromatic aldehydes gave the best results. Sterically hindered β-ketoesters resulted in lower reaction yields. The reaction was carried out under heterogeneous catalysis to allow easy recovery of the product from the reaction mixture and recycling of the catalyst. The heterogeneity of the reaction was confirmed by carrying out a hot filtration test.

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“…HF (40 %) medium via Biginelli multicomponent reaction (Scheme 144). [242] Using a similar strategy, Konkala et al applied novel bioglycerol-based sulphonic acid functionalized carbon catalyst in modified Biginelli reaction to access 3,4-dihydropyrimidine derivatives (Scheme 144). [243] The catalyst was recycled and reused four times without apparent loss of activity.…”

Section: Putilova Et Al Reported the Use Of Ionic Liquid [Bmim][bfmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

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Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives

Cited by 9 publications

References 25 publications

[EMIM]AlCl₄‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives

[EMIM]AlCl₄‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives

Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones via a Three-Component Biginelli Reaction

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

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Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives

Cited by 9 publications

References 25 publications

[EMIM]AlCl4‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives

[EMIM]AlCl4‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives

Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones via a Three-Component Biginelli Reaction

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

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[EMIM]AlCl₄‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives

[EMIM]AlCl₄‐ionic liquid catalyzed mechanochemically assisted synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐one and thione derivatives