Catalyst-free UV<sub>365</sub>-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities

Dutta, Arup; Rahman, Noimur; Kumar, John Elisa; Rabha, Jintu; Phukan, Tridip; Nongkhlaw, Rishanlang

doi:10.1080/00397911.2020.1825741

Cited by 24 publications

(9 citation statements)

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“…[31] In the three-component synthesis of pyranopyrazoles, Riad et al (1989) had earlier mixed acetoacetanilide and α-cyanocinnamonitrile derivatives at room temperature for 2 h in the presence of triethylamine to yield Michael adduct, which further treated with hydrazine hydrate under reflux to produce pyrano[2,3-c]pyrazole derivatives (Route 4). [96] Another threecomponent reaction for the synthesis of pyranopyrazole derivatives has also been reported by Amer et al (2021) via the condensation reaction of pyrazolone, aldehyde derivative, and malononitrile in the presence of ZnO nanoparticle (Route 5), [97] N-methylmopholine, [43] MPSMA@Fe 3 O 4 , [98] triethylbenzylammonium chloride (TEBA), [99] D,L-Proline, [100] Nd-SM, [101] [Amb]Lprolinate, [102] nano-TiO 2 /H 14 [NaP 5 W 30 O 110 ], [103] nano-titania sulfuric acid (15-nm TSA), [104] UV light, [105] tungstate sulfuric acid (TSA), [106] meglumine, [107] KF-montmorillonite, [108] sulfamic acid, [109] HClO 4 À SiO 2 nanoparticles, [110] H 14 [NaP 5 W 30 O 110 ], [111] Saba Farooq is a postdoctoral researcher at the MgFeCrO 4 NPs, [112] Fe 3 O 4 @GOÀ N-(pyridin-4-amine) nanofilms, [113] Fe 3 -xTixO 4 @TMSP@TBAAsp, [114] Ag 3 [PMo 12 O 40 ] • nH 2 O, [115] γ-Fe 2 O 3 @Cu 3 Al-LDH-TUD, [116] hexade cyltrimethyl ammonium bromide (HTMAB), [117] Fe 3 O 4 @GOQDÀ O-(propane-1-sulfonic acid), [118] piperidine, [119,120] L-proline-melamine, [121] {Fe 3 O 4 @SiO 2 @-(CH 2 ) 3 -thiourea dioxide-SO 3 H/HCl}, [122] POM@Dy-PDA, [123] P4VPyÀ CuI, [124] [Et 2 NH(CH 2 ) 2 CO 2 H][AcO] [125] and NB-Fe 3 O 4 @SiO 2 @CPTMO@DEA-SO 3 H. [126] An ionic liquid of triethylammonium acetate (TEAA) has also been us...…”

Section: Synthesis Of Pyranopyrazole and Its Derivativesmentioning

confidence: 99%

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Farooq,

Ngaini

2024

ChemistrySelect

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Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives. Pyranopyrazole is an important structural unit in heterocyclic chemistry and is useful in pharmaceutical and agrochemical industries. The pyranopyrazole‐based compounds are known in the agricultural industry as herbicides, fungicides, and insecticide agents and in medicinal fields as antimicrobial, anticancer, and antiHIV agents. Despite its wide range of applications, the synthesis of pyranopyrazole has several limitations such as the cost of reagents, potential environmental risks, harsh reaction conditions, longer reaction times, laborious workup procedures, and unsatisfactory yields. However, many studies have been recently reported on the synthesis of pyranopyrazoles using mild, green, and environmentally friendly methods that also give higher yields. Different catalysts and conditions have been reported for the synthesis of pyranopyrazole using four, three, and two components. Among these, four‐component synthesis is commonly reported by using benzaldehyde, hydrazine derivatives, ethyl acetoacetate and malononitrile due to the commercial availability and stability of the reagents. This review summarized the recent synthesis of pyranopyrazole i. e., mono‐ and bis‐pyranopyrazole derivatives via four‐, three‐ and two‐component‐based reactions. Mono‐ and bis‐pyranopyrazole derivatives varied due to the number of pyranopyrazole units that contributed to play an important role in increasing the binding interaction and biological activities beneficial for pharmaceutical industries.

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Section: Synthesis Of Pyranopyrazole and Its Derivativesmentioning

confidence: 99%

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Farooq,

Ngaini

2024

ChemistrySelect

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“…A series of tetrahydropyran derivatives was synthesized in H 2 O: EtOH (1:1) solvent system under eight lamps of UV365 light sources under air-bubbling condition for 45-60 min at room temperature without using any photocatalyst. [44] The authors employed a number of precursors like dimedone, cyclohexadione, isatin, and pyrazolone to study the efficacy of the reaction. The advantages of developed protocol are catalyst-free conditions, reaction at RT (room temperature), short reaction S C H E M E 5 Synthesis of pyrans containing heterocyclic derivatives using catalyst-free approach time, excellent yields (90%-97%), high functional group tolerance, wide substrate scope, and so forth (Scheme 7).…”

Section: Catalyst-free Synthesismentioning

confidence: 99%

An overview of recent advances in the catalytic synthesis of substituted pyrans

Agarwal¹,

Sethiya²,

Soni³

et al. 2022

Applied Organom Chemis

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Substituted pyrans (4H‐Chromenes) are the most significant structural scaffolds in synthetic and medicinal chemistry. They are found in an array of natural products, medicines, and phytochemical compounds, bearing an explicit of pharmacological activities. The structural importance of substituted pyrans has elicited a huge upsurge in the field of synthesis and biology. Different synthetic approaches of 4H‐chromene scaffolds have been discussed systematically to emphasize their significance in the scientific world. The present article summarizes the different synthetic strategies of substituted pyran derivatives via acid‐base catalysis, ionic liquids, nanomaterials, deep eutectic solvents, bio‐based, visible light, metal catalyzed, and so forth developed in the last decade. Moreover, this article will definitely contribute to the scientific world for developing synthetically and biologically important pyran analogs.

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“…Thus, from the viewpoint of synthetic chemists, these reactions contribute significantly to synthesizing heterocyclic compounds in organic chemistry. [1][2][3][4][5][6][7][8][9][10][11] Chromenes and pyrans are considerably important heterocyclic compounds attracting the attention of scientists due to their various significant biological effects, including anticancer, [12][13][14] antibacterial, [15,16] antioxidant, [17] antimycobacterial [18,19] and anti-epileptic [20] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

Salmalian,

Mahmoodi,

Sheykhan

2023

ChemistrySelect

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A new method for synthesizing chromene derivatives as an essential class of heterocyclic compounds has been reported. This research described synthesizing and identifying three new organic salt catalysts based on phosphate moieties. Among the synthesized new phosphate‐based organic salt catalysts, disodium ethyl (phenyl) amino phosphate (DSEAP) plays an essential role and reusable catalyst for the preparation of chromene derivatives under different reaction conditions following the principles of green chemistry. Cost‐effectiveness, non‐toxicity and easy availability are among the salient features of this environmentally friendly catalyst. Furthermore, the catalyst was satisfactorily recycled up to four times without significant performance degradation in the yield of synthesized chromenes. X‐ray diffraction (XRD), infrared spectroscopy (FT‐IR), thermal gravimetric analysis (TGA), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) were employed to illustrate the structural and morphologic characteristics of the catalysts. Some synthesized chromene derivatives, including 4I and 4P, showed good antibacterial and biological antioxidant activity compared to the standard drug, respectively. In this research, DSEAP was used as a heterogeneous catalyst in performing one‐pot 3MCRs of aryl aldehyde, an active methylene group e. g. ethyl acetoacetate or diethyl malonate and 5,5‐dimethyl‐1,3‐cyclohexanedione.

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Catalyst-free UV₃₆₅-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities

Cited by 24 publications

References 58 publications

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

An overview of recent advances in the catalytic synthesis of substituted pyrans

One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

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Catalyst-free UV365-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities

Cited by 24 publications

References 58 publications

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

An overview of recent advances in the catalytic synthesis of substituted pyrans

One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

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Catalyst-free UV₃₆₅-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities