A critical review on recent trends on pharmacological applications of pyrazolone endowed derivatives

Journal of Molecular Structure, Journal Year: 2022, Volume and Issue: 1262, P. 133044 - 133044

Published: April 11, 2022

Language: Английский

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Enantioselective Synthesis of Spiro Heterocyclic Compounds Using a Combination of Organocatalysis and Transition‐Metal Catalysis

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(7)

Published: Jan. 26, 2023

Abstract Over the last ten years, combination of organocatalysis with transition metal (TM) catalysis has become one most important toolboxes used for synthesizing optically pure compounds containing chiral quaternary centers, including spiro heterocyclic molecules. The dominant method in enantioselective synthesis based on synergistic includes aminocatalysis and NHC catalysis, as already established covalent organocatalytic strategies. Another area widely combined TM producing enantiomerically enriched is non‐covalent dominated by phosphoric acids, thiourea, squaramide derivatives. This review article aims to summarize methods constructing spirocyclic heterocycles a catalysis.

Language: Английский

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Pyridinium Ylide-Mediated Diastereoselective Synthesis of Spirocyclopropanyl-pyrazolones via Cascade Michael/Substitution Reaction

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 8230 - 8242

Published: May 14, 2024

We have devised a highly diastereoselective formal [2 + 1] annulation reaction of arylidene/alkylidine-pyrazolones with in situ-generated supported as well standard pyridinium ylides to construct spirocyclopropanyl-pyrazolones. The cascade approach exhibits wide range functional group tolerance, gram-scale capability, and substrate versatility. A diverse spirocyclic cyclopropanes was synthesized extensively both mediators, the pyridine reused subsequent cycles. Density theory calculations confirmed formation spirocyclopropane lower energy pathway.

Language: Английский

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The literature of heterocyclic chemistry, part XXII, 2022

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Visible-light-induced C–S bond formation of pyrazolin-5-ones with thioureas to pyrazol-4-yl carbamimidothioates

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 580, P. 115086 - 115086

Published: April 8, 2025

Language: Английский

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Phosphine‐Catalyzed (3 + 2) Annulation of δ‐Hydroxyl Allenylic Alcohols with Pyrazolinone‐Derived Ketimines

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(3)

Published: Jan. 1, 2025

Abstract The phosphine‐catalyzed (3 + 2) annulation reaction of δ ‐hydroxyl‐substituted allenylic alcohols with pyrazolinone‐derived ketimines has been developed, giving a variety spiro dihydropyrrole‐dihydropyrazolone derivatives in high yields good diastereoselectivities. Various unsaturated and diverse worked well under mild conditions, 31 examples were provided up to 97% yield >20:1 diastereoselectivity. scale‐up further transformations the product successfully acheived, three derivation experiments showed feasibility product. These results revealed that current could be useful tool for synthesis derivatives. In addition, we also investigated asymmetric version this ketimines, 86% ee chiral was obtained use bifunctional phosphine catalyst.

Language: Английский

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Stereodivergent construction of [6.5]-spirocycles bearing three contiguous stereogenic centers by Pd-catalyzed [4+2] annulations

Chem Catalysis, Journal Year: 2023, Volume and Issue: 3(7), P. 100669 - 100669

Published: June 19, 2023

Language: Английский

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Design, Spectroscopic, and Crystal Structural Characterization of New Pyrazolone-Based Schiff Bases: Molecular Docking Investigations against SARS-Covid-19 Main Proteases (PDB Ids: 6LU7 and 7TLL)

Polycyclic aromatic compounds, Journal Year: 2022, Volume and Issue: 43(10), P. 8933 - 8945

Published: Dec. 20, 2022

New pyrazolone-based Schiff bases were synthesized and characterized by various spectroscopic analytical techniques such as 1H-NMR, FTIR, UV − Vis spectroscopy elemental analysis. Crystal structures of two the Schiff-base (SB) compounds obtained single-crystal X-ray crystallography (SCXRC). The target from condensation 4-acetyl-3-methyl-1-phenyl-5-pyrazolone with 1,2-diaminobenzene (SB1), 4-methyl-1,2-diaminobenzene (SB2), 4,5-dimethy-1,2-diaminobenzene (SB3). Molecular docking modeling was used to study interactions these molecules SARS-CoV-2 virus main proteases (PDB ids: 6LU7 7TLL). estimated free binding energies (EFBE) for all three SBs better than standard drugs favipiravir dexamethasone. Besides, order EFBE −7.68 (SB3)> −7.36 (SB1)> −7.06 kcal.mol−1 (SB2) −10.42 −10.05 −9.69 7TLL. SB3 showed best both that is discussed based on structure–function relationship.

Language: Английский

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Fast, highly enantioselective, and sustainable fluorination of 4-substituted pyrazolones catalyzed by amide-based phase-transfer catalysts

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(9), P. 2226 - 2233

Published: Jan. 1, 2023

Highly enantioselective and sustainable fluorination of 4-substituted pyrazolones has been developed by amide-based phase-transfer catalysts.

Language: Английский

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Access to Spiropyrazolone-butenolides through NHC-Catalyzed [3 + 2]-Asymmetric Annulation of 3-Bromoenals and 1H-Pyrazol-4,5-diones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6890 - 6900

Published: May 11, 2023

The stereoselective synthesis of spirocyclic pyrazolin-5-ones by N-heterocyclic carbene (NHC) organocatalysis has been less studied so far. For this reason and considering the interest class compounds, here, we present NHC-catalyzed [3 + 2]-asymmetric annulation β-bromoenals 1H-pyrazol-4,5-diones that achieves to produce chiral spiropyrazolone-butenolides. is general for aryl heteroaryl β-bromo-α,β-unsaturated aldehydes 1,3-disubstituted pyrazolones. spirobutenolides have obtained in good yields (up 88%) enantioselectivities 97:3 er). This constitutes first described example using pyrazoldiones as starting materials spiro compounds.

Language: Английский

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