Iron-catalyzed four-member multicomponent reaction for assembly of (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones

Zhang, Zhiguo; Zhang, Lianqiang; Duan, Xinyu; Yan, Xiangqian; Yan, Yan; Li, Qingfeng; Liu, Tongxin; Zhang, Guisheng

doi:10.1016/j.tet.2015.07.039

Cited by 18 publications

(7 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An iron‐catalysed multicomponent methodology for the potentially bioactive ( E )‐6‐arylvinyl‐3,4‐dihydropyrimidin‐2(1 H )‐ones 149 from acetoamides 147 , urea 148 and aryl aldehydes 30 was established. [ 85 ] Substrate scope studies revealed the applicability of this method to both electron‐donating and electron‐withdrawing group substituted aryl aldehydes (Scheme 57).…”

Section: Classificationmentioning

confidence: 99%

Recent advances in the iron‐catalysed multicomponent reactions

Saranya

Aneeja

Neetha

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

Iron‐catalysed reactions are widely used in organic synthesis owing to its benefits over other metals. Among the important organic reactions, multicomponent reactions play a significant role due to its greener aspects like high atom economy, minimal amount of by‐product, economic feasibility etc. For the past few years, iron‐catalysed multicomponent reactions have attracted the attention of several chemists which lead to the invention of some fine chemistry. The majority of iron‐catalysed multicomponent reactions results in the synthesis of heterocyclic compounds having biologically active natural products, pharmaceutical etc. These developments in the iron‐catalysed multicomponent reactions are the focus of this review. This is the first review in this topic which covers the literature up to 2020, and it encompasses the different methods for the synthesis of acyclic, carbocyclic and heterocyclic compounds.

show abstract

Section: Classificationmentioning

confidence: 99%

Recent advances in the iron‐catalysed multicomponent reactions

Saranya

Aneeja

Neetha

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…A subsequent Biginelli reaction then generates compound 2 (see Figure 2). This reaction pathway differs from the pathway suggested by Zhang et al (2015), who proposed that product 1 is an intermediate in the reaction that was conducted using the Lewis acid catalyst, FeCl 3 ·6H 2 O [17]. Besides the different catalyst, the 1,3-dicarbonyl component used by Zhang was an acetoacetanilide derivative.…”

Section: Resultsmentioning

confidence: 83%

Ethyl (E)-4-(2,4-Dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Suwito

Zulianto

Haq

et al. 2017

Molbank

View full text Add to dashboard Cite

Abstract:A new compound belonging to the "heterostilbene" derivative, namely ethyl (E)-4-(2,4-dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2), has been successfully synthesized as an unprecedented side product of the Biginelli reaction between 2,4-dimethoxybenzaldehyde, ethyl acetoacetate and urea, employing PTSA as catalyst in reflux conditions and using ethanol as solvent. The molecular structure of compound (2) was established by FTIR, HRESIMS, 1D and 2D NMR.

show abstract

“…The Biginelli reaction [ 27 , 28 , 29 ] is an important MCR [ 30 ] because the products exhibit a wide range of biological activities. An acid-catalyzed Biginelli reaction involving a one-pot three component condensation of furochromone carbaldehyde ( 1 ), Curcumin ( 2 ), and urea/thiourea gave compounds 8a , b ( Scheme 5 ).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

et al. 2018

View full text Add to dashboard Cite

Curcumin, a widely utilized flavor and coloring agent in food, has been shown to demonstrate powerful antioxidant, antitumor promoting and anti-inflammatory properties in vitro and in vivo. In the present work, synthesis of new heterocyclic derivatives based on Curcumin was studied. Compound 3 was synthesized via the reaction of furochromone carbaldehyde (1) with Curcumin (2) using pipredine as catalyst. Also, novel, 4,9-dimethoxy-5H-furo [3, 2-g] chromen-5-one derivatives 4a–d, 6a–d, 7, 8a–d, 9 and 10 were synthesized by the reactions of furochromone carbaldehyde (1) with different reagents (namely: appropriate amine 3a–d, appropriate hydrazine 5a–d, hydroxylamine hydrochloride, urea/thiourea, malononitrile, malononitrile with hydrazine hydrate). The structure of the synthesized products had been confirmed from their spectroscopic data (IR, 1H-NMR, 13C-NMR and mass spectra). In the present investigation, the newly synthesized products were screened using the MTT colorimetric assay for their in vitro inhibition capacity in two human cancer cell lines (hepatocellular carcinoma (HEPG2) and breast cancer (MCF-7) as well as the normal cell line (human normal melanocyte, HFB4) in comparison to the known anticancer drugs: 5-flurouracil and doxorubicin. The anticancer activity results indicated that the synthesized products 4c and 8b showed growth inhibition activity against HEPG2 cell line and synthesized products 4b and 8a showed growth inhibition activity against MCF-7, but with varying intensities in comparison to the known anticancer drugs, 5-flurouracil and doxorubicin. Cyclin dependent kinase 2 (CDK2), a major cell cycle protein, was identified as a potential molecular target of Curcumin. Furthermore, Curcumin induced G1 cell cycle arrest, which is regulated by CDK2 in cancer cells. Therefore, we used molecular modelling to study in silico the possible inhibitory effect of CDK2 by Curcumin derivatives as a possible mechanism of these compounds as anticancer agents. The molecular docking study revealed that compounds 4b, 8a and 8b were the most effective compounds in inhibiting CDk2, and, this result was in agreement with cytotoxicity assay.

show abstract

Iron-catalyzed four-member multicomponent reaction for assembly of (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones

Cited by 18 publications

References 47 publications

Recent advances in the iron‐catalysed multicomponent reactions

Recent advances in the iron‐catalysed multicomponent reactions

Ethyl (E)-4-(2,4-Dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

Contact Info

Product

Resources

About