Synthesis and X-ray crystal structures of polyfunctionalized 4H-chromene derivatives via tricomponent reaction with Knoevenagel adducts as intermediates in aqueous medium

Zanin, Lucas Lima; Jimenez, David Esteban Quintero; Jesus, Matheus Pereira de; Diniz, Luan F.; Ellena, Javier; Porto, André Luiz Meleiro

doi:10.1016/j.molstruc.2020.129226

Cited by 9 publications

(2 citation statements)

References 26 publications

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“…On the other hand, having an electron-donating para-methoxy substituent (in 7) further increases the RMSD value to 0.116 Å. All bond angles and distances are comparable to those of closely related fused pyranyl 52 and dihydropyridinyl 53 derivatives in the literature.…”

Section: Synthetic Consideration and Spectroscopic Analysis Of Compou...supporting

confidence: 69%

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

Zamisa

Ngubane

Adeleke

et al. 2022

Crystal Growth & Design

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Four 2-amino-4-(aryl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (Series I) and three 2-amino-1phenyl-7,7-dimethyl-5-oxo-4-(aryl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (Series II) derivatives were formed via multicomponent microwave reactions as racemic mixtures. The solid-state IR spectra revealed bands in the region between 3190 and 3414 cm −1 attributed to the amino functional group's asymmetric, symmetric, and bending overtone vibration modes. Furthermore, the IR spectra of some of the compounds in each series were similar and this served as an indication of similar structural features in the solid state. This was confirmed via single-crystal X-ray diffraction. A detailed survey of the related 2-amino-3-carbonitrile derivatives in the Cambridge Structural Database revealed 12 classical intermolecular hydrogen-bonding motifs involving the amino functional group. The vast variation in the hydrogen bonding motifs was found to be caused by the type of group bonded to the 4H-pyran (in Series I) or dihydropyridine (in Series II) moiety. In this work, an unprecedented hydrogen bonding motif comprising a non-classical hydrogen bond acceptor was found in one instance. For both Series I and II, the N−H•••N and N−H•••O hydrogen bonds were investigated using noncovalent interaction (NCI) plots and molecular pairwise energy calculations. The contributions of reciprocal N•••H and O•••H contacts (attributed to N−H•••N and N−H•••O, respectively) toward the Hirshfeld surface range between 9.9 and 15.3% in Series I and between 10.8 and 15.0% in Series II. In addition, the compounds showed moderate to good binding affinity to calf thymus DNA (CT-DNA) with intrinsic binding constants (K b ) between 8.00 × 10 4 and 5.00 × 10 5 M −1 for Series I compounds and between 6.60 × 10 4 and 1.45 × 10 5 M −1 for Series II. A relationship was established between the reciprocal N•••H to O•••H contributions ratio from the Hirshfeld surface analysis and K b . Molecular docking studies of each compound's respective enantiomers into DNA were done using canonical−DNA dodecamer (B-DNA) as a model for CT-DNA. The compounds were found to interact with DNA via a minor groove-binding mode. The S-enantiomer for most of the compounds bound favorably compared to their respective R-enantiomers. The ratio of calculated ΔG for the DNA binding of the Renantiomer to that of the S-enantiomer (ΔG R /ΔG S ) follows the same positive trend as the experimental K b value for each compound in Series I while a negative trend was observed for Series II. Finally, a relationship between the Hirshfeld surface analysis and calculated ΔG values was also established in this work.

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Section: Synthetic Consideration and Spectroscopic Analysis Of Compou...supporting

confidence: 69%

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

Zamisa

Ngubane

Adeleke

et al. 2022

Crystal Growth & Design

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“… Method Reaction conditions Yield (%) Reusability Refs. A Neat, 100 °C; 1h; Basic conditions 100 1 45 B HAHS’ ionic liquid, 0.75 h 99 1 46 C Chitosan Based Heterogeneous Catalyses: ethanol: 3 h 95 1 47 D Lithium perchlorate In acetonitrile at 20 °C ; 3 h; Electrolysis; 92 1 48 E Triethylamine In water at 50 °C; Microwave irradiation; 92 1 49 F Silica gel for 0.0333333 h; microwave irradiation; 91 1 50 G Amine In N,N-dimethyl-formamide at 120 °C ; microwave irradiation; 79 1 51 H Meglumine In ethanol; water at 20 °C; for 0.0833333 h; 97 1 57 I Zinc(II) oxide In ethanol; water at 20 °C ; 3 h; 95 3 52 J Ferrocene-Functionalized Dithiocarbamate Zinc In ethanol at 20 °C ; for 2 h; 95 ...…”

Section: Resultsmentioning

confidence: 99%

Magnet-responsive choline carbomer ionogels as a versatile and recyclable catalyst for one-pot synthesis of benzopyran in water

Shojaee,

Azizi,

Mirjafary

et al. 2023

Sci Rep

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Ionogels are gaining popularity as a potential replacement for volatile organic solvents in various processes, such as catalysts, electrochemistry, spectroscopy, and medicinal chemistry, due to their low toxicity, high thermal stability, and good solubility. Magnet-responsive ion gels with high magnetic susceptibility are promising and can be used as catalysts, sensors, and MRI contrast agents. Herein, we fabricated simple and novel magnet choline carbomer ionogels using a precipitation-deposition method with carbomers and choline hydroxide. The morphology and structure of the resulting ionogels were analyzed using various characterization techniques, including FTIR, EDX, TGA, and SEM spectroscopy. These magnet ionogels were effective catalysts for a one-pot, three-component synthesis of benzopyran derivatives, providing mild reaction conditions, environmental friendliness, and good to excellent (78–96%) yields within a short reaction time (1–2 h). Additionally, the magnet ionogels were easily recyclable, and they could be reused up to five times without catalytic deactivation.

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Metal-free Knoevenagel Condensation and Other Condensation Reactions (Perkin, Darzens)

Khaligh,

Titinchi,

Abbo

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Synthesis and X-ray crystal structures of polyfunctionalized 4H-chromene derivatives via tricomponent reaction with Knoevenagel adducts as intermediates in aqueous medium

Cited by 9 publications

References 26 publications

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

Magnet-responsive choline carbomer ionogels as a versatile and recyclable catalyst for one-pot synthesis of benzopyran in water

Metal-free Knoevenagel Condensation and Other Condensation Reactions (Perkin, Darzens)

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