Iridium-Catalyzed, Highly Selective Allylation of Pyrazolones for the Convenient Construction of Adjacent Stereocenters DOI
Shixiang Sun, Yuqi Zhang, Martin G. Banwell

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 22, 2024

This paper describes an iridium-catalyzed allylation of ring-fused pyrazolones that proceeds with excellent regio-, diastereo- and enantio-selectivities. The approach exploits unactivated, racemic allylic alcohols as a source allyl building blocks. Asymmetric syntheses series biologically relevant, chiral highlight the utility methodology. use Cu(OTf)

Language: Английский

A critical review on recent trends on pharmacological applications of pyrazolone endowed derivatives DOI
Ghulam Mustafa, Muhammad Zia‐ur‐Rehman, Sajjad Hussain Sumrra

et al.

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

Published: April 11, 2022

Language: Английский

Citations

63
Enantioselective Synthesis of Spiro Heterocyclic Compounds Using a Combination of Organocatalysis and Transition‐Metal Catalysis DOI Creative Commons
Martin Kamlar, Michal Urban, Ján Veselý

et al.

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

Citations

16
Pyridinium Ylide-Mediated Diastereoselective Synthesis of Spirocyclopropanyl-pyrazolones via Cascade Michael/Substitution Reaction DOI
Akanksha Kumari,

Dhirajkumar Jitendrabhai Patanvadiya,

Anshul Jain

et al.

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

Citations

5
Recent advances in the catalytic asymmetric construction of axially chiral azole-based frameworks DOI
Weiwei Luo, Yu Zhang,

Meijun Ming

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6819 - 6849

Published: Jan. 1, 2024

This review highlights recent advances in the atroposelective preparation of axially chiral azole derivatives, emphasizing mechanistic insights and synthetic applications development this class five-membered heterocyclic frameworks.

Language: Английский

Citations

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

Zeqing Duan,

Min Liu

et al.

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

Citations

0
The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

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

Published: Jan. 1, 2025

Language: Английский

Citations

0
Visible-light-induced C–S bond formation of pyrazolin-5-ones with thioureas to pyrazol-4-yl carbamimidothioates DOI
Renhua Zheng, Haichang Guo, Xiu-Rong Hu

et al.

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

Published: April 8, 2025

Language: Английский

Citations

0
Assessment of pyrazolone derivatives as a new class of cyclooxygenase-2 and aflatoxigenic fungal inhibitors DOI
V. Meenatchi,

So Yeon Won,

Zainab M. Almarhoon

et al.

International Journal of Biological Macromolecules, Journal Year: 2025, Volume and Issue: 311, P. 143903 - 143903

Published: May 5, 2025

Language: Английский

Citations

0
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) DOI
Maryam Esfahani, Liana Ghasemi, Mahdi Behzad

et al.

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

Citations

14
Stereodivergent construction of [6.5]-spirocycles bearing three contiguous stereogenic centers by Pd-catalyzed [4+2] annulations DOI Creative Commons

Zhan-Cai Ma,

Lin-Wen Wei,

Song Liu

et al.

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

Published: June 19, 2023

Language: Английский

Citations

8