N-Vinylation of Imidazole and Benzimidazole with a Paramagnetic Vinyl Bromide

Úr, Györgyi; Fekete, Gergely Gulyás; Hideg, Kálmán; Kálai, Tamás

doi:10.3390/m980

Cited by 2 publications

(2 citation statements)

References 26 publications

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“…Compound 234 can be regarded as a paramagnetic analog of the sulfonamide drug, sulfadiazine. Compound 39 reaction with 2-aminobenzimidazole produced 1,1,3,3-tetramethyl-1H-benzimidazo[1,2]pyrrolo[3,4-e]pyrimidin-2yloxyl radical 235, with formation of Schiff-base 236 [92] (Scheme 42).…”

Section: Nitroxides Fused With Six-membered Het-erocyclesmentioning

confidence: 99%

Synthesis and Application of Stable Nitroxide Free Radicals Fused with Carbocycles and Heterocycles

Bognár

Úr

Sár

et al. 2019

COC

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Stable nitroxide free radicals have traditionally been associated with 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) or its 4-substituted derivatives as relatively inexpensive and readily accessible compounds with limited possibilities for further chemical modification. Over the past two decades, there has been a resurgence of interest in stable free radicals with proper functionalization tuned for various applications. The objective of this review is to present recent results with synthetic methodologies to achieve stable nitroxide free radicals fused with aromatic carbocycles and heterocycles. There are two main approaches for accessing stable nitroxide free radicals fused with arenes, e.g., isoindoline- like nitroxides: further functionalization and oxidation of phthalimide or inventive functionalization of pyrroline nitroxide key compounds. The latter also offers the constructions of versatile heterocyclic scaffolds (furan, pyrrole, thiophene, 1,2-thiazole, selenophene, pyrazole, pyrimidine, pyridine, pyridazine, 1,5-benzothiazepine) that are fused with pyrroline or tetrahydropyridine nitroxide rings. The possible applications of these new stable nitroxide free radicals, such as covalent spin labels and noncovalent spin probes of proteins and nucleic acids, profluorescent probes, building blocks for construction of dual active drugs and electroactive materials, and substances for controlled free radical polymerization, are discussed.

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Section: Nitroxides Fused With Six-membered Het-erocyclesmentioning

confidence: 99%

Synthesis and Application of Stable Nitroxide Free Radicals Fused with Carbocycles and Heterocycles

Bognár

Úr

Sár

et al. 2019

COC

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“…In this sequence, Stephanie Hesse and co‐worker in 2007 reported the Buchwald‐Hartwig Csp 2 −N amination of β ‐chloroacroleins by lactams and heteroarylamines ( Scheme 1). [6] Further, in 2018 Tamas Kalai and co‐worker reported N‐vinylation of azoles with a paramagnetic vinyl bromide ( Scheme 1), [7] while both the reports employed expensive Pd(OAc) 2 as catalyst, other expensive reagents and rigorous conditions. Hence, there is a strong need to developed a more economical and sustainable protocols.…”

Section: Introductionmentioning

confidence: 99%

Novel Ferrocenyl‐azole Derivatives: Synthesis, DFT Calculation and Unlocking the Anticancer Potential

Tomar,

Kumar,

Sharma

et al. 2024

Eur J Org Chem

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Herein, a series of novel ferrocenyl/phenyl/thiophenyl‐azoles was disclosed by vinylic amination of ferrocenyl/phenyl/thiophenyl substituted β‐chloro cinnamaldehydes and acrylonitriles. A highly economical and robust chalcogen‐stabilized iron selenide carbonyl cluster Fe3Se2(CO)9 worked as an efficient catalyst under aerobic conditions. The amination of ferrocenyl/phenyl/thiophenyl substituted β‐chloro‐vinylic Csp2‐Cl with azole derivatives was fully established and fabrication of the Csp2‐N bond was completely supported by various spectral analysis. Moreover, wide range of substrates with functionally different azoles were investigated for the present reaction and good to excellent transformation was recorded. Some of the selected ferrocenated azole derivatives were screened for anti‐cancer activity against the prostate cancer cells (PC‐3) and found to be highly active at low concentration of 5.77µM with IC50 value. Furthermore, HOMO and LUMO levels and energy gap of some selected compounds were calculated by the density functional theory (DFT).

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N-Vinylation of Imidazole and Benzimidazole with a Paramagnetic Vinyl Bromide

Cited by 2 publications

References 26 publications

Synthesis and Application of Stable Nitroxide Free Radicals Fused with Carbocycles and Heterocycles

Synthesis and Application of Stable Nitroxide Free Radicals Fused with Carbocycles and Heterocycles

Novel Ferrocenyl‐azole Derivatives: Synthesis, DFT Calculation and Unlocking the Anticancer Potential

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