Synthesis of Novel Chalcone Analogues of Ferrocene Biarenes

Song, Qingbao; Li, Xiaonian; Shen, Tianhua; Yang, Shang‐Dong; Gen-rong, Qiang; Wu, Xiaoli; Ma, Yan

doi:10.1081/scc-120026317

Cited by 19 publications

(5 citation statements)

References 12 publications

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“…This reaction has been widely used for the synthesis of hydroxyl-substituted chalcones, typically with good to excellent yields (60–90%). A group of ferrocenylchalcones has been synthesized under the common base (sodium hydroxide) condition (Table , entry 1) . In some cases, an increase in temperature is required, and the base condition also requires modification.…”

Section: Synthesismentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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Privileged structures have been widely used as an effective template in medicinal chemistry for drug discovery. Chalcone is a common simple scaffold found in many naturally occurring compounds. Many chalcone derivatives have also been prepared due to their convenient synthesis. These natural products and synthetic compounds have shown numerous interesting biological activities with clinical potentials against various diseases. This review aims to highlight the recent evidence of chalcone as a privileged scaffold in medicinal chemistry. Multiple aspects of chalcone will be summarized herein, including the isolation of novel chalcone derivatives, the development of new synthetic methodologies, the evaluation of their biological properties, and the exploration of the mechanisms of action as well as target identification. This review is expected to be a comprehensive, authoritative, and critical review of the chalcone template to the chemistry community.

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Section: Synthesismentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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“…Ferrocenecarboxaldehyde, acetylferrocene, ethynyltrimethylsilane, 4'-bromoacetophenone, 4-bromobenzaldehyde and 1-iodo-4-nitrobenzene were purchased from Aldrich and used without further purification. The synthesis of 3-ferrocenyl-1-(4'-bromophenyl), A, 4-ethynylacetophenone, C, 4-ethynylbenzaldehyde, D, and [RuCl(dppe) 2 ]OTf were previously reported [41,58,59]. The already reported compound 1-ferrocenyl-3-(4'-bromophenyl)-prop-2-en-1-one [53], B, was obtained by the following modified method: 246 mg of KOH (4.38 mmol), was dissolved in 40 mL of methanol and 10 mL of water.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and characterization of new mono and bi-nuclear ferrocene derivatives connected via a cross-conjugated prop-2-en-1-one bridge

Escobar

Gutierrez

Verdugo

et al. 2017

Journal of Organometallic Chemistry

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“…k 2 Equation (7) simplifies to a second-order rate law in which deprotonation of 4 r is the rate-determining step [Eq. (8)]. For k À1 @ k 2 Equation (7) turns into a rate law in which rapid deprotonation pre-equilibrium precedes rate-determining protonation of contact ion pair 5 r to give allenol 6 r [Eq.…”

Section: A C H T U N G T R E N N U N G (Hetero)aryl Halide 1 Propargymentioning

confidence: 99%

“…Aryl substituents with various electronic natures (entries 1-5), even with further halide substituents, are tolerated and can be carried through the sequence. Furthermore, electroneutral and electron-rich heterocyclic substituents (entries [6][7][8][9][10][11] are fully compatible with the CIR, and also alkenyl-substituted propargyl alcohols (entries [12][13][14] give the expected enones in good yields. As a restriction it became evident that propargyl alcohols with alkyl substituents do not furnish enones, and the reaction halted at the stage of the coupled propargyl alcohol.…”

Section: Introductionmentioning

confidence: 99%

“…By virtue of [2p + 2p] photocycloaddition, some chalcones are photochromic in merocyanine-containing polymer matrices. [7] While 1-ferrocenyl 3-biaryl propenones are novel types of nonlinear optical (NLO) chromophores, [8] photorefractive polymers doped with push/pull-substituted chalcones show remarkable electrooptic responses, [9] and NLO properties of silylated chalcones in sol-gel matrices have been studied. [10] In synthetic heterocyclic chemistry, as a consequence of the bifunctional Michael system, 1,3-diaryl prop-2-en-1-ones are important three-carbon building blocks.…”

Section: Introductionmentioning

confidence: 99%

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Coupling–Isomerization Synthesis of Chalcones

Braun

Ansorge

Müller

2006

Chemistry A European J

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The Sonogashira coupling of electron-deficient (hetero)aryl halides 1 and (hetero)aryl or alkenyl 1-propargyl alcohols 2 does not terminate at the stage of the expected internal propargyl alcohols, but rather gives rise to the formation of alpha,beta-unsaturated ketones 3 with a variety of acceptor substituents. This new domino reaction, a coupling-isomerization reaction (CIR), can be rationalized as a sequence of rapid Pd/Cu-catalyzed alkynylation followed by a slow amine-base-catalyzed propargyl alcohol-enone isomerization. Performing the CIR in deuterated protic solvents or with a selectively deuterated propargyl alcohol revealed that the base-catalyzed isomerization step proceeds through a formal 1,3-H shift with minimal H/D exchange with the surrounding solvent. Additionally, 19F NMR kinetic measurements on the isomerization step with the fluorinated propargyl alcohol 4 r support the mechanistic rationale.

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Synthesis of Novel Chalcone Analogues of Ferrocene Biarenes

Cited by 19 publications

References 12 publications

Chalcone: A Privileged Structure in Medicinal Chemistry

Chalcone: A Privileged Structure in Medicinal Chemistry

Synthesis and characterization of new mono and bi-nuclear ferrocene derivatives connected via a cross-conjugated prop-2-en-1-one bridge

Coupling–Isomerization Synthesis of Chalcones

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