Regioselective Synthesis of N-Aryl Pyrazoles from Alkenyl Sulfoxonium Ylides and Aryl Diazonium Salts DOI

Ramesh Kumar Vishwakarma,

Raju Sen,

Shalu Deshwal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

A convenient and practical method has been developed for synthesizing various N-aryl pyrazoles from vinyl sulfoxonium ylides diazonium salts. When using 1,3-disubstituted ylides, the reaction selectively yields 1,3,5-trisubstituted pyrazoles. On other hand, employing 2,3-disubstituted results in formation of 1,3,4-trisubstituted The proceeds through novel aryl diazene-derived ylide. Furthermore, this efficiently produces aniline derivatives a one-pot transformation. takes place under transition metal-free, mild conditions easily accessible starting materials, making it approach generating pharmaceutical chemistry.

Language: Английский

Recent Developments Towards the Synthesis of Triazole Derivatives: A Review DOI Creative Commons
Issam Ameziane El Hassani,

Khouloud Rouzi,

Anouar Ameziane El Hassani

et al.

Organics, Journal Year: 2024, Volume and Issue: 5(4), P. 450 - 471

Published: Oct. 24, 2024

The triazole scaffold is a crucial component of heterocyclic chemistry, serving as basic building block in organic synthesis, materials science, and medicinal chemistry. Triazole five-membered ring composed three nitrogen atoms two carbon atoms, it exists isomeric forms: 1,2,3-triazole 1,2,4-triazole. Compounds featuring the are important heterocycles known for their diverse biological activities, including antimicrobial, antiproliferative, antimalarial, anticonvulsant, anti-inflammatory, antineoplastic, antiviral, analgesic, anticancer properties. As result, derivatives have attracted significant attention from researchers. This review aims to provide thorough overview published studies on synthesis derivatives, highlighting various methods obtaining moiety. These include classical approaches well microwave ultrasound-assisted techniques.

Language: Английский

Citations

3

Coordination chemistry of 4-aminopyrazole: Structure and physicochemical properties of cobalt(II) chlorido complexes, and amino group reactivity towards a ketone to yield an imine bond DOI Creative Commons
Kiyoshi Fujisawa,

Keigo Ageishi,

K. Iwai

et al.

Inorganica Chimica Acta, Journal Year: 2024, Volume and Issue: 572, P. 122283 - 122283

Published: July 26, 2024

An outline of the in situ construction a coordination polymer by reacting mononuclear cobalt(II) complex, functionalised with an amine substituent, acetone is given. The methodology involved 4-amino-3,5-diisopropyl-1-pyrazole (denoted as L1pzHNH2) precursor, putative linker molecule. Reaction ligand anhydrous chloride, yielded four-coordinated chlorido [CoCl2(L1pzHNH2)2]. When complex was reacted acetone, polymer, [CoCl2{L1pzHN=C(CH3)2}]n, imine bond, obtained. complexes were characterised various spectroscopic techniques. X-ray crystallography shows [CoCl2(L1pzHNH2)2]·2(thf) to comprise tetrahedrally coordinated centre donors being two and pyrazolyl-N atoms. Similarly, [CoCl2{L1pzHN=C(CH3)2}]n features Cl2N2 donor set defining approximately tetrahedral geometry imine-N derived from pyrazolyl ring symmetry related exocyclic atom result that one-dimensional helical topology formed. uncoordinated precursor molecule, L1pzHNH2, formation confirmed 1H NMR measured (CD3)2CO solution. However, for CDCl3 solution, 70:30 equilibrium between established. It concluded nucleophilicity group enhanced binding pyrazole nitrogen [CoCl2(L1pzHNH2)2]·2(thf), thereby favouring irreversible formation. facile solid-state also correlates reduced solubility structure organic solvents.

Language: Английский

Citations

2

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps DOI Creative Commons

Ignaz Betcke,

A. C. Götzinger, Maryna N. Kornet

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2024 - 2077

Published: Aug. 16, 2024

Pyrazoles are rarely found in nature but traditionally used the agrochemical and pharmaceutical industries, while other areas of use also actively developing. However, they have numerous applications. The search for new efficient syntheses these heterocycles is therefore highly relevant. modular concept multicomponent reactions (MCR) has paved a broad alley to heteroaromatics. advantages over traditional methods broader scope increased efficiency reactions. In particular, multistep pyrazoles considerably been extended by MCR. Progress made cyclocondensation 1,3-dielectrophiles that generated situ. Limitations regioselectivity with 1,3-dicarbonyls were overcome addition-cyclocondensation α,β-unsaturated ketones. Embedding 1,3-dipolar cycloadditions into one-pot process additionally developed concise pyrazoles. MCR strategy allows concatenating classical condensation-based methodology modern cross-coupling radical chemistry, as well providing versatile synthetic approaches This overview summarizes most important based on ring-forming sequences flashlight fashion.

Language: Английский

Citations

2

Antibacterial and Antifungal Pyrazoles Based on Different Construction Strategies DOI

Muneeb Ur Rehman,

Fang He,

Xi Shu

et al.

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 282, P. 117081 - 117081

Published: Nov. 20, 2024

Language: Английский

Citations

2

Regioselective Synthesis of N-Aryl Pyrazoles from Alkenyl Sulfoxonium Ylides and Aryl Diazonium Salts DOI

Ramesh Kumar Vishwakarma,

Raju Sen,

Shalu Deshwal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

A convenient and practical method has been developed for synthesizing various N-aryl pyrazoles from vinyl sulfoxonium ylides diazonium salts. When using 1,3-disubstituted ylides, the reaction selectively yields 1,3,5-trisubstituted pyrazoles. On other hand, employing 2,3-disubstituted results in formation of 1,3,4-trisubstituted The proceeds through novel aryl diazene-derived ylide. Furthermore, this efficiently produces aniline derivatives a one-pot transformation. takes place under transition metal-free, mild conditions easily accessible starting materials, making it approach generating pharmaceutical chemistry.

Language: Английский

Citations

2