Synthesis, crystal structure, hydrogen bond patterns and Hirshfeld surface analysis of (S)-5-(4-hydroxybenzyl)-imidazolidine-2,4‑dione

Delgado, Gerzón E.; Mora, Asiloé J.; Narea, Pilar; Chacón, Cecília; Marroquín, Gustavo; Hernández, Benjamín; Cisterna, Jonathan; Brito, Iván

doi:10.1016/j.molstruc.2021.131757

Cited by 2 publications

(2 citation statements)

References 35 publications

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“…26 Preparation of 5-(4-Hydroxybenzyl)imidazolidine-2,4-dione (2b). 27 L-Tyrosine (0.05 mol) and KOCN (5.0 g) were suspended in 30 mL of water. Pyridine (ca.…”

Section: ■ Conclusionmentioning

confidence: 99%

CuF₂/MeOH-Catalyzed N³-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

et al. 2023

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An efficient and practical N-arylation of hydantoins with substituted aryl/heteroaryl boronic acids has been established, assisted by CuF 2 /MeOH under the base and ligand-free conditions at room temperature and open air. The protocol is general, and various N-arylated hydantoins have been prepared in excellent yields with exclusive regioselectivity. The CuF 2 /MeOH combination was explored further to furnish selective N 3 -arylation of 5fluorouracil nucleosides. The efficiency of the protocol was also demonstrated with the gram-scale synthesis of the marketed drug, Nilutamide. A mechanistic study based on density functional theory calculations revealed that both hydantoin and MeOH are crucial for the generation of catalytically active copper species in the reaction process, in addition to their role as a reactant and solvent, respectively. The proposed reaction mechanism indicated that selective N 3 -arylation of hydantoin is favorable in MeOH, which helps initiate the catalytic cycle by forming a square-planner Cu(II) complex where strong hydrogen-bond interactions are observed. This study is expected to improve the understanding of Cu(II)-catalyzed oxidative N-arylation reactions and for the de novo design and development of Cu-catalyzed coupling reactions.

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“…26 Preparation of 5-(4-Hydroxybenzyl)imidazolidine-2,4-dione (2b). 27 L-Tyrosine (0.05 mol) and KOCN (5.0 g) were suspended in 30 mL of water. Pyridine (ca.…”

Section: ■ Conclusionmentioning

confidence: 99%

CuF₂/MeOH-Catalyzed N³-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

et al. 2023

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“…Following our investigation on hydantoin and thiohydantoin derivative compounds (Seijas et al, 2010;Delgado et al, 2020Delgado et al, , 2021Delgado et al, , 2022Hernández et al, 2021) in previous work, we reported the X-ray powder diffraction data for the polymorph I of 1-methylhydantoin MH-I (Delgado et al, 2015) in the Powder Diffraction File database with code PDF-00-066-1563 (Gates-Rector and Blanton, 2019) and report now the X-ray powder data for the two new polymorphs MH-II and MH-III.…”

Section: Introductionmentioning

confidence: 99%

X-ray powder diffraction data for the second and third polymorphs of 1-methylhydantoin

Delgado

2022

Powder Diffr.

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X-ray powder diffraction data for the two new polymorphs of 1-methylhydantoin, C4H6N2O2, are reported. The polymorph II (MH-II) crystallizes in the orthorhombic system with space group Pna21 [a = 19.0323(7) Å, b = 3.91269(8) Å, c = 6.8311(7) Å, Z′ = 1, Z = 4, unit cell volume V = 508.70(3) Å3. Polymorph III (MH-III) crystallizes in the orthorhombic system with space group P212121 [a = a = 7.82427(5), b = 9.8230(5), c = 20.2951(4), Z′ = 3, Z = 12, unit cell volume V = 1563.5(1) Å3]. All measured lines, in each case, were indexed and are consistent with the space group.

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Synthesis, crystal structure, hydrogen bond patterns and Hirshfeld surface analysis of (S)-5-(4-hydroxybenzyl)-imidazolidine-2,4‑dione

Cited by 2 publications

References 35 publications

CuF₂/MeOH-Catalyzed N³-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

CuF₂/MeOH-Catalyzed N³-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

X-ray powder diffraction data for the second and third polymorphs of 1-methylhydantoin

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Synthesis, crystal structure, hydrogen bond patterns and Hirshfeld surface analysis of (S)-5-(4-hydroxybenzyl)-imidazolidine-2,4‑dione

Cited by 2 publications

References 35 publications

CuF2/MeOH-Catalyzed N3-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

CuF2/MeOH-Catalyzed N3-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

X-ray powder diffraction data for the second and third polymorphs of 1-methylhydantoin

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Product

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CuF₂/MeOH-Catalyzed N³-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

CuF₂/MeOH-Catalyzed N³-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight