An improved microwave‐assisted facile one‐pot synthesis of novel pyrazolylphosphonates via Knoevenagel‐phospha‐Michael protocol DOI

Sara Mahdjoub,

Chamseddine Derabli, Muhammet Yıldırım

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(7), P. 1045 - 1056

Published: May 8, 2024

Abstract In this study, a highly effective microwave‐assisted method employing multicomponent domino Knoevenagel/phospha‐Michael reaction has been established. This approach facilitates the synthesis of novel set pyrazolylphosphonate derivatives in good yields by combining aryl aldehydes with pyrazolones and trialkylphosphites, utilizing piperidine as Bronsted base catalyst. All pyrazolylphosphonates have characterized means IR, 1 H‐NMR, 13 C‐NMR, HRMS analyses physical methods. protocol can be its eco‐friendly nature, exceptional efficiency terms product yields, short times.

Language: Английский

Recent Advances in Pyridine Scaffold: Focus on Chemistry, Synthesis, and Antibacterial Activities DOI Creative Commons
Md. Badrul Islam, Md. Inshaful Islam,

Nikhil Nath

et al.

BioMed Research International, Journal Year: 2023, Volume and Issue: 2023(1)

Published: Jan. 1, 2023

Multidrug-resistant (MDR) pathogens have created a fatal problem for human health and antimicrobial treatment. Among the currently available antibiotics, many are inactive against MDR pathogens. In this context, heterocyclic compounds/drugs play vital role. Thus, it is very much essential to explore new research combat issue. Of nitrogen-bearing compounds/drugs, pyridine derivatives of special interest due their solubility. Encouragingly, some newly synthesized found inhibit multidrug-resistant S. aureus (MRSA). Pyridine scaffold bearing poor basicity generally improves water solubility in pharmaceutically potential molecules has led discovery numerous broad-spectrum therapeutic agents. Keeping these mind, we reviewed chemistry, recent synthetic techniques, bacterial preventative activity since 2015. This will facilitate development pyridine-based novel antibiotic/drug design near future as versatile with limited side effects next-generation therapeutics.

Language: Английский

Citations

56
Zn(II)-Catalyzed Multicomponent Sustainable Synthesis of Pyridines in Air DOI
Subhasree Pal, Siuli Das, Subhajit Chakraborty

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3650 - 3665

Published: Feb. 28, 2023

Herein, we report a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines using alcohols as the primary feedstock NH4OAc nitrogen source. Using well-defined air-stable Zn(II)-catalyst, 1a, featuring redox-active tridentate azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (La), wide variety unsymmetrical 2,4,6-substituted were prepared by three-component coupling secondary with NH4OAc. Catalyst 1a is equally compatible four-component coupling. Unsymmetrical also via alcohol two different A series up to 67% yield 1-phenylpropan-1-one or 1,2-diphenylethan-1-one The 1a-catalyzed reactions proceeded efficiently upon replacing corresponding ketones, producing desired in higher yields shorter reaction time. few control experiments performed unveil mechanistic aspects, which indicates that active participation aryl-azo ligand during catalysis enables Zn(II)-complex act an efficient catalyst for present multicomponent reactions. Aerial oxygen acts oxidant dehydrogenation alcohols, H2O H2O2 byproducts.

Language: Английский

Citations

18
Recent developments in the synthesis of azaindoles from pyridine and pyrrole building blocks DOI
Damoder Reddy Motati, Radhika Amaradhi, Thota Ganesh

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 8(3), P. 466 - 513

Published: Nov. 26, 2020

The azaindole framework is ubiquitous in bioactive natural products and pharmaceuticals. This review highlights the synthetic approaches to azaindoles with advantages limitations, mechanistic pathways biological importance.

Language: Английский

Citations

36
A concise review on some synthetic routes and applications of pyridine scaffold compounds DOI Open Access

Shaban A. A. Abdel-Raheem,

Adel M. Kamal El‐Dean,

Mokhtar A. Abd ul‐Malik

et al.

Current Chemistry Letters, Journal Year: 2021, Volume and Issue: 10(4), P. 337 - 362

Published: Jan. 1, 2021

Different methods for the synthesis of pyridine derivatives as well chemical reactivity profiles and structures these substances are reviewed. The utility compounds precursors is emphasized in many heterocycles that pharmacologically active organic agrochemicals. This review results from a literature survey containing some synthetic applications derivatives.

Language: Английский

Citations

28
Selective Synthesis of Substituted Pyridines and Pyrimidines through Cascade Annulation of Isopropene Derivatives DOI
Jian Li, Jiaming Li,

Runfa He

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(8), P. 1620 - 1625

Published: Feb. 23, 2022

Diverse substituted pyridines and pyrimidines with high selectivity were obtained using a concise efficient protocol developed herein. The reaction proceeds via metal-free cascade annulation of isopropene derivatives. Using derivatives as C3 synthons, NH4I the "N" source, formaldehyde or dimethyl sulfoxide carbon this realizes formation intermolecular C-N C-C bonds.

Language: Английский

Citations

14
NH4OAc-Promoted Domino Route to Hydroxyarylated Unsymmetrical Pyridines under Neat Conditions DOI

Meher Prakash,

Santosh K. Gudimella,

Rajni Lodhi

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 85(4), P. 2151 - 2167

Published: Dec. 25, 2019

A new metal-, oxidant-, and solvent-free ecofriendly domino method has been established for modular synthesis of a diverse range medicinally promising hydroxyarylated unsymmetrical pyridines in good to high chemical yields with an excellent regioselectivity. This process involves N-sulfonyl ketimines as C,N-binucleophiles, enolizable ketones, aromatic/heteroaromatic aldehydes using ammonium acetate ideal promoter under neat conditions, which creates two C-C bonds one C-N bond. Notably, the neutral reaction conditions are mild enough tolerate functionalities cover variety substrates, thus bestowing powerful avenue access tri- tetrasubstituted including carbo- heterocyclic fused ones. Interestingly, practical, scalable, high-yielding pyridylphenol derivatives was successfully accomplished by our unique method.

Language: Английский

Citations

20
Primary amine C–N bond cleavage for the synthesis of multi-substituted pyridine and pyrrole derivatives DOI
Ruiqin Zhang,

Yuxin Ding,

Renchao Ma

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(3), P. 780 - 785

Published: Dec. 9, 2022

Synthesis of multi-substituted pyridines and pyrroles was established involved C-N bond cleavage new C–N C–C formation. The adjacent to the primary carbon 1,2-diamino-2-methylpropane selectively cleaved.

Language: Английский

Citations

12
Sources, Transformations, Syntheses, and Bioactivities of Monoterpene Pyridine Alkaloids and Cyclopenta[c]pyridine Derivatives DOI Creative Commons
Xuejian Zhang,

Feiyan Tao,

Cui Tao

et al.

Molecules, Journal Year: 2022, Volume and Issue: 27(21), P. 7187 - 7187

Published: Oct. 24, 2022

Monoterpene pyridine alkaloids (MTPAs) are derived from iridoid glycosides (IGs). The common molecular structure of MTPAs is the ring, while some them have a cyclopenta[c]pyridine skeleton. Some compounds containing this potentially bioactive medicinal agents. In paper, seven drug candidates (A-G), ninety natural source products (1-90), thirty-seven synthesized (91-127), as well twenty-six key intermediates (S1-S26) were summarized. We categorized five types and one type in all. Additionally, their possible genetic pathways proposed. Then, chemical transformation, biotransformation, synthesis, bioactivity derivatives analyzed Cyclopenta[c]pyridine can be concisely chirally synthesized, they shown potentials with antibacterial, insecticidal, antiviral, anti-inflammatory, neuropharmacological activities.

Language: Английский

Citations

11
Sustainable Four-Component Annulation for the Synthesis of 2,3,4,6-Tetraarylpyridines DOI

Yuxin Ding,

Renchao Ma,

Xu‐Qiong Xiao

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(5), P. 3897 - 3906

Published: Feb. 17, 2021

A one-pot, four-component annulation of 2,3,4,6-tetraarylpyridines from aromatic aldehydes, methyl ketones, diaryl ethanones, and ammonium acetate is described. The reaction features high functional group compatibility in air under solvent-free conditions without any additive only water as the nontoxic byproduct, providing a strategy for facile, economical, eco-friendly construction multiaryl-substituted pyridines simple readily available reactants.

Language: Английский

Citations

14
A Metal-Free Visible-Light Photoredox Construction and Direct C–H Functionalization of Pyridines: Green Synthesis of Polysubstituted Picolinaldehydes DOI

Qun-Liang Zhang,

Qinqin Yu, Li Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 17244 - 17248

Published: Nov. 22, 2021

The development of a novel environmental benign and sustainable synthetic method for highly efficient construction direct C-H functionalization N-heterocycles remains pivotal central research topic organic medicinal chemistry. Herein, visible-light-enabled biomimetic aza-6π electrocyclization assembly diverse pyridines further tandem Minisci-type reaction were developed. A broad spectrum polysubstituted picolinaldehydes readily constructed with high efficacy good functional group tolerance under metal- oxidant-free conditions.

Language: Английский

Citations

14