Nicotine‐based ionic liquid supported on magnetic nanoparticles: An efficient and recyclable catalyst for selective one‐pot synthesis of mono‐ and bis‐4H‐pyrimido[2,1‐b]benzothiazoles

Alishahi, Nasrin; Nasr‐Esfahani, Mahboobeh; Mohammadpoor‐Baltork, Iraj; Tangestaninejad, Shahram; Mirkhani, Valiollah

doi:10.1002/aoc.5681

Cited by 18 publications

(4 citation statements)

References 70 publications

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“…1 HNMR (DMSO- d 6 ): 5 (ppm) 9.04 [s, 1H, OH], 8.03 [d, 1H, C7- H, J = 8 Hz], 7.96 [d, 2H, C2-H, C6-H, J = 8 Hz], 7.90 [d, 1H, C4-H, J = 4 Hz], 7.47-7.52 [m, 1H, C5-H], 7.37-7.41 [m, 1H, C6-H], 6.95 [d, 2H, C3 -H, C5 -H, J = 8 Hz]. 13 CNMR (DMSO- d 6 ): δ 171.94(the carbon which is directly bonded to nitrogen and sulfur) ( 23 ), 166.45, 162.75, 151.38, 133.79, 132.72, 126.47, 125.80, 124.83, 122.21, 116.09. m/z: 254.05 (EI), yield 64%.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, antioxidant activity, and density functional theory study of some novel 4-[(benzo[d]thiazol-2-ylimino)methyl]phenol derivatives

Asgarshamsi

Fassihi

Hassanzadeh

et al. 2021

Research in Pharmaceutical Sciences

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Background and purpose: Radicals produced by Fenton and Haber-Weiss reactions play detrimental roles in our body. Some oxidized proteins as toxic configurations are identified in amyloid-β deposits. These deposits mostly occur in conditions, such as Alzheimer’s disease. Here, we report the synthesis, evaluation of the antioxidant activity, and implementation of density functional theory (DFT) calculations of some4- [(benzo[ d ]thiazol-2-ylimino) methyl]phenol derivatives. The aim of this study was to provide a comparative theoretical-experimental approach to explain the antioxidant activities of the compounds. Experimental approach: Compounds were synthesized by the reaction between para hydroxybenzaldehyde and aminobenzothiazole derivatives. The scavenging activity of the compounds was evaluated. Various electronic and energetic descriptors such as high occupied molecular orbital and low unoccupied molecular orbital energy gaps, bonding dissociation enthalpy of OH bond, ionization potential, electron affinity, hardness, softness, and spin density of the radical and neutral species were calculated. DFT calculations with B3LYP hybrid functional and 6-311++ G** basis set in the polarizable continuum model were utilized to obtain these descriptors. Findings/Results: Ascorbic acid showed the best DPPH scavenging activity. However, 4d and 4c showed promising antioxidant activity. The values of EHOMO for 4c and 4d were closer to zero, thus, they showed the best scavenging activities. The computational results were in accordance with the experimental ones. The energetic descriptors indicated that the sequential proton loss-electron transfer mechanism is preferred over other mechanisms. Conclusion and implication: Antioxidant activity of 4-[(Benzo[ d ]thiazol-2-ylimino) methyl]phenol derivatives confirmed by experimental and theoretical documents proves them as novel antioxidants against amyloid-β based disease.

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Section: Resultsmentioning

confidence: 99%

Synthesis, antioxidant activity, and density functional theory study of some novel 4-[(benzo[d]thiazol-2-ylimino)methyl]phenol derivatives

Asgarshamsi

Fassihi

Hassanzadeh

et al. 2021

Research in Pharmaceutical Sciences

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“…The chemicals were purchased from Fluka and Merck chemical companies. 5-aryl-1,3,4-thiadiazol-2-amines, 3-(5-amino-1,3,4-thiadiazol-2-yl)-2 H -chromen-2-one, 5,5′-(butane-1,4-diylbis(sulfanediyl))bis(1,3,4-thiadiazol-2-amine) and 2,2′-(butane-1,4-diylbis(oxy))dibenzaldehyde were prepared similar to the reported methods 57 – 60 . Melting points were determined using a Stuart Scientific SMP2 apparatus.…”

Section: Methodsmentioning

confidence: 99%

Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl2⋅6H2O deep eutectic solvent

Korbekandi,

Mohammadpoor-Baltork,

Moghadam

et al. 2024

Sci Rep

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In this research, a new Lewis acid-based deep eutectic solvent (LA-DES) was synthesized using diphenhydramine hydrochloride and CoCl2·6H2O, (2[HDPH]:CoCl42−), and identified by FT-IR and 1HNMR techniques. The physicochemical properties of this LA-DES, such as thermal behavior, thermal stability, and solubility in common solvents were also investigated. The catalytic ability of 2[HDPH]:CoCl42− was ascertained in the efficient synthesis of a novel array of thiadiazolo[2,3-b]quinazolin-6-one scaffolds via a one-pot three-component reaction of dimedone/1,3-cyclohexanedione, aldehydes, and 5-aryl-1,3,4-thiadiazol-2-amines/3-(5-amino-1,3,4-thiadiazol-2-yl)-2H-chromen-2-one under solvent-free conditions. This catalyst was also successfully utilized for the synthesis of mono- and bis-thiadiazolo[2,3-b]quinazolin-6-ones from dialdehydes or bis-1,3,4-thiadiazol-2-amine. The simplicity of enforcement, short reaction time, avoidance of toxic organic solvents, scalability of the synthesis procedure, excellent atom economy, high reaction mass efficiency, and low E-factor are other outstanding advantages of this newly developed method. Furthermore, due to the convenient recovery and reuse of LA-DES, this protocol is economically justified and environmentally friendly.

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“…38 The chemistry of heterocyclic compounds, which deals with the properties, synthesis, and applications of this class of compounds, is considered an important branch of organic chemistry. 39,40 On the other hand, research on organosulfur chemistry (compounds containing S element) is one of the most important topics in medicinal, pharmaceutical and industrial chemistry. 41,42 Benzothiazoles are a class of aberrant compounds that have a benzene ring fused to a thiazole ring.…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄@ABA-aniline-CuI nanocomposite as a highly efficient and reusable nanocatalyst for the synthesis of benzothiazole-sulfide aryls and heteroaryls

Sun

Liu

et al. 2023

RSC Adv.

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Nicotine‐based ionic liquid supported on magnetic nanoparticles: An efficient and recyclable catalyst for selective one‐pot synthesis of mono‐ and bis‐4H‐pyrimido[2,1‐b]benzothiazoles

Cited by 18 publications

References 70 publications

Synthesis, antioxidant activity, and density functional theory study of some novel 4-[(benzo[d]thiazol-2-ylimino)methyl]phenol derivatives

Synthesis, antioxidant activity, and density functional theory study of some novel 4-[(benzo[d]thiazol-2-ylimino)methyl]phenol derivatives

Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl2⋅6H2O deep eutectic solvent

Fe₃O₄@ABA-aniline-CuI nanocomposite as a highly efficient and reusable nanocatalyst for the synthesis of benzothiazole-sulfide aryls and heteroaryls

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Nicotine‐based ionic liquid supported on magnetic nanoparticles: An efficient and recyclable catalyst for selective one‐pot synthesis of mono‐ and bis‐4H‐pyrimido[2,1‐b]benzothiazoles

Cited by 18 publications

References 70 publications

Synthesis, antioxidant activity, and density functional theory study of some novel 4-[(benzo[d]thiazol-2-ylimino)methyl]phenol derivatives

Synthesis, antioxidant activity, and density functional theory study of some novel 4-[(benzo[d]thiazol-2-ylimino)methyl]phenol derivatives

Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl2⋅6H2O deep eutectic solvent

Fe3O4@ABA-aniline-CuI nanocomposite as a highly efficient and reusable nanocatalyst for the synthesis of benzothiazole-sulfide aryls and heteroaryls

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Fe₃O₄@ABA-aniline-CuI nanocomposite as a highly efficient and reusable nanocatalyst for the synthesis of benzothiazole-sulfide aryls and heteroaryls