1,10‐Phenanthrolin‐1‐ium Trinitromethanide (1,10‐PHTNM) as a Nano Molten Salt Catalyst With Y‐Aromatic Counter Ion: Applications for Synthesis of Organic Compounds

Dashteh, Mohammad; Baghery, Saeed; Zolfigol, Mohammad Ali; Bayat, Yadollah; Asgari, Asiye

doi:10.1002/slct.201803402

Cited by 16 publications

(6 citation statements)

References 55 publications

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“…White solid; R f = 0.35 (pure EtOAc); mp = 214–217 °C (lit. mp = 210–215 °C); − 1 H NMR (CDCl 3 , 400 MHz): δ 10.91 (br s, 2H), 7.29 (t, J = 7.72 Hz, 2H), 7.21 (d, 7.2 Hz, 1H), 7.14 (d, 8.0 Hz, 2H), 6.04 (d, 2H), 5.73 (s, 1H), 2.27 (s, 6H); 13 C NMR (CDCl 3 , 100 MHz): δ 135.3, 128.5, 126.7, 126.4, 103.5, 102.8, 34.7, 19.7; MS (APCI) m / z : [M + H] + calcd for C 19 H 17 O 6 340, found 341.…”

Section: Methodsmentioning

confidence: 99%

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

et al. 2022

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A simple, straightforward, and energy-efficient greener route for the synthesis of a series of biologically interesting functionalized 1,1-dihomoarylmethane scaffolds has been developed in the presence of meglumine as an efficient and eco-friendly organo-catalyst via one-pot pseudo-three-component reaction at room temperature. Following this protocol, it is possible to synthesize 1,1-dihomoarylmethane scaffolds of an assortment of C–H activated acids such as dimedone, 1,3-cyclohexadione, 4-hydroxy-6-methyl-2-pyrone, 4-hydroxycoumarin, and 1-phenyl-3-methyl-pyrazolone. The salient features of the present green protocol are mild reaction conditions, good to excellent yields, operational simplicity, easy isolation of products, no cumbersome post treatment, high atom economy, and low E-factor. In addition, this chemistry portrays several green advantages including the reusability of reaction media and product scalability, which makes protocol sustainably efficient. Additionally, several control experiments such as protection of catalyst reactive site, D 2 O exchange, and 1 H NMR studies revealed possible pathways for meglumine-promoted reactions. Inspired by the natural physiological environment of 1,1-dihomoarylmethane scaffolds, we reconnoitered the biological profile of our compounds and synthesized compounds that were promising for their antiproliferative and antibacterial activities.

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Section: Methodsmentioning

confidence: 99%

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

et al. 2022

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“…Dashteh and co-authors [70] have prepared 1,10-Phenanthrolin-1-ium trinitromethanide (1,10-PHTNM) as a nano molten salt with aromatic counter ion and used it as a catalyst (15 mg) in the synthesis of bisdimedone by the reaction of dimedone with various aldehydes in the aqueous solution at 60 C. This protocol comprised with several advantages like the high yields of product (50%-91%), short reaction time, simple work-up, easy purification of product, and reusability of catalyst up to six runs (Scheme 8: Method 6).…”

Section: Synthesis Of Bisdimedones Using Simple Organic Compounds Based Catalystsmentioning

confidence: 99%

Advancement in synthetic strategies of bisdimedones: Two decades study

Teli¹,

Sahiba²,

Sethiya³

et al. 2021

Journal of Heterocyclic Chem

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Bisdimedones have emerged as an important and versatile moiety in the field of synthetic and medicinal chemistry. It is screened as a precursor for the synthesis of several heterocycles such as acridinediones, xanthenediones, thioxanthenes, and benzopyrans that exhibited immense pharmacological as well as industrial applications. Its extensive characteristics have attracted the scientists to develop various protocols for the synthesis of bisdimedones and their derivatives from the reaction of dimedone with several aldehydes under different environmental conditions using various types of catalysts. This review encapsulates the recent progress in the synthesis of bisdimedone derivatives under several reaction protocols such as the use of nanoparticles, ionic liquids, metal salts, simple organic compounds, and catalyst-free conditions, and so forth in the last 20 years.

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“…In current times, a combination of ionic liquid and molten salt has gained much interest in organic synthetic chemistry due to their synergistic effect on the catalytic process. Therefore, Dashteh and group [120] synthesized nano molten salt, 1,10‐phenanthrolin‐1‐ium trinitromethanide (1,10‐PHTNM) with Y‐aromatic counter ion and applied it for an effective catalysis of acridinediones synthesis process using dimedone, ammonium acetate and substituted benzaldehyde in aqueous green medium at 80 °C. This novel catalyst worked as a proton sponge due to the presence of two nitrogen atoms having non‐bonded repulsions because of peri ‐effect and also hold high electron charge density.…”

Section: Synthesis Of Acridine‐18‐dione Derivativesmentioning

confidence: 99%

Acridine‐1,8‐diones: Synthesis and Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2021

ChemistrySelect

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The unpretentious features of acridine‐1,8‐diones viz. presence of N‐heteroatom, electronic behavior, acridine ring skeleton and wide possibilities of diversified substitution, bichromophoric structure and interaction ability with various proteins, make them an interesting scaffold of heterocyclic, medicinal and industrial chemistry. A tremendous development in the field of acridinediones in terms of synthetic strategies, bioactivity, industrial and other applicability has been explored in past four decades. In this perspective, an overview has been given on the state‐of‐art discoveries for the synthesis and biological applications of acridine‐1,8‐diones from 1980 to 2020. The study highlighted the history, chemistry and properties of these derivatives and provided deep insights into the synthetic protocols using various catalysts and techniques like nano‐catalyst, ionic‐liquids, microwave, ultrasound etc. under varied conditions along with biological activity against many lethal diseases. Finally, the respective prospects and limitations to these systems have been addressed. Furthermore, attempts have been done to bring many outstanding researches together and express the significance of acridine‐1,8‐diones through several aspects. We hope that the article shall deliver an impetus to explore further the synthetic values and mechanistic puzzles of acridinedione moiety and to design more promising hybrid multi‐targeted drugs and other industrial composites for the goodness of humanity

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1,10‐Phenanthrolin‐1‐ium Trinitromethanide (1,10‐PHTNM) as a Nano Molten Salt Catalyst With Y‐Aromatic Counter Ion: Applications for Synthesis of Organic Compounds

Cited by 16 publications

References 55 publications

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

Advancement in synthetic strategies of bisdimedones: Two decades study

Acridine‐1,8‐diones: Synthesis and Biological Applications

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