Overview of Phenylhydrazine‐Based Organic Transformations DOI Open Access
Pragati Kushwaha,

Ayush Bhardwaj,

Rashi

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 10(1)

Published: Dec. 30, 2024

Abstract Phenylhydrazines, comprised of a phenyl group attached with hydrazine unit, contribute potentially to organic synthetic transformations. Because the myriad applications, last decade has witnessed considerable upsurge interest perform various reactions catalyzed/mediated/promoted by phenylhydrazines. Some these have shown high regioselectivity in short reaction time under mild conditions. The emergence innumerable transformations utilizing phenylhydrazine unleashed numerous openings for development diverse heterocyclic scaffolds. Given importance this valuable chemical entity, review highlights methodologies Moreover, present article will considerably synthesis as well pharmaceutical chemistry. Academically, be interesting and informative researchers attempting develop new routes structures.

Language: Английский

Transition metals-catalyzed amination of biomass feedstocks for sustainable construction of N-heterocycles DOI
Qiong Yan, Xu Wu, Hao Jiang

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 502, P. 215622 - 215622

Published: Dec. 26, 2023

Language: Английский

Citations

75
Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods DOI Creative Commons

Rita Bernadett Vlocskó,

Guoshu Xie, Béla Török

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(10), P. 4153 - 4153

Published: May 17, 2023

Recent advances in the environmentally benign synthesis of aromatic N-heterocycles are reviewed, focusing primarily on application catalytic methods and non-traditional activation. This account features two main parts: preparation single ring N-heterocycles, their condensed analogs. Both groups include compounds with one, more N-atoms. Due to large number protocols, this focuses providing representative examples feature available methods.

Language: Английский

Citations

17
Zn(II)‐Stabilized Azo‐Anion Radical Catalyzed Sustainable C−C Bond Formation: Regioselective Alkylation of Fluorene, Oxindole, and Indoles DOI
Subhasree Pal, Amit Kumar Guin, Subhajit Chakraborty

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(10)

Published: Feb. 7, 2024

Abstract Herein we report a sustainable approach for the alkylation of ketones, 9 H ‐fluorene, oxindole, and indole using alcohols as alkylating agent catalyzed by well‐defined air‐stable zinc catalyst ( 1 ) tridentate redox non‐innocent arylazo ligand, 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline L ). 2–3 mol % efficiently produces substituted α‐alkylated 9‐alkylated fluorenes, C3 ‐alkylated oxindoles, indoles in moderate to good isolated yields. In aerial condition, formation bis(indolyl)methane (BIMs) derivatives were observed when subjected primary alcohols. A few drug molecules containing BIMs prepared The exhibited chemoselectivity during functionalization fluorene with oleyl alcohol β‐citronellol. control experiments, including deuterium labeling performed unveil reaction mechanism indicate that one‐electron reduced azo‐anion radical species [ ]‐formed situ, acts active catalyst. All events occur at redox‐active aryl‐azo which reservoir hydrogen electrons throughout catalytic cycle, keeping Zn(II)‐center template.

Language: Английский

Citations

8
[3 + 2] Cycloaddition Reaction of Vinylsulfonium Salts with Hydrazonoyl Halides: Synthesis of Pyrazoles DOI

Wen-Jing Luo,

Xiuwen Liang,

Maizhuo Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10066 - 10076

Published: July 2, 2024

An efficient [3 + 2] cycloaddition reaction between in situ generated nitrile imines from hydrazonoyl halides and vinylsulfonium salts is developed. The are demonstrated to be a new class of partner for conduct the reaction. process provides concise method construction pyrazole derivatives under mild conditions with broad substrate scope, good product yields, high regioselectivity.

Language: Английский

Citations

5
Arene Binuclear Ru(II)-Promoted Sustainable Synthesis of Substituted Pyrazoles from Alcohols via Acceptorless Dehydrogenative Annulation DOI
Veerappan Tamilthendral, Rengan Ramesh

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4162 - 4167

Published: May 31, 2023

We report a selective and sustainable synthesis of substituted pyrazoles via an eco-friendly acceptorless dehydrogenative annulation (ADA) greener alcohols, malononitrile, various aromatic hydrazides by newly synthesized binuclear Ru(II) p-cymene complexes. A discrete set complexes are fabricated structurally characterized analytical, spectral, single-crystal X-ray diffraction methods. Further, the catalytic effectiveness is explored for construction 5-amino-4-cyano-N-aroylpyrazoles (34 examples) under mild conditions produces H2O/H2 as only byproduct. sequence polysubstituted has been constructed in 62-95% yield using 1 mol % catalyst loading. Probable intermediates detected reaction have isolated confirmed nuclear magnetic resonance electrospray ionization mass spectrometry studies. Expediently, therapeutically significant gout medicine "allopurinol" analogue derived successfully from 5-amino-4-cyano-N-aroylpyrazoles.

Language: Английский

Citations

12
Electrochemical cascade pyrazole annulation and C-H halogenation for the synthesis of 4-halopyrazoles DOI Creative Commons
Haijin Guo, Yunyun Liu, Jie‐Ping Wan

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 1, 2023

The synthesis of 4-halo-functionalized pyrazoles by electrochemical cascade reactions between N,N-dimethyl enaminones and proper hydrazine reagents in the presence a halogen source is realized at room temperature. work provides tunable efficient accesses to 4-chloro- 4-bromopyrazoles aqueous THF (tetrahydrofuran) without using any transition metal reagent.

Language: Английский

Citations

10
Current Advances in Synthesis of Pyrazole Derivatives: An Approach Toward Energetic Materials DOI
Jaime Portilla

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 2, 2024

ABSTRACT Pyrazole derivatives are strategic structural motifs due to their proven utility in preparing chemicals biological, pharmaceutical, photophysical, technological, and industrial fields; therefore, syntheses of pyrazole‐containing compounds highly desirable. Some nitrogen‐rich pyrazoles, specifically nitrated posing high density moderate thermal stability, have been used as energetic since a amount energy is stored structures that can be released quickly with detonation power under external stimuli (i.e., thermal, impact, friction). These good capacity sensitivity explosives, propellants, pyrotechnics applications eco‐friendly ways. Therefore, this contribution focuses on recent illustrative examples regarding the (i) synthesis reactivity especially works last decade, highlighting (ii) analyze scope.

Language: Английский

Citations

3
Monoacetylated bishydroperoxide-derived singlet molecular oxygen-mediated oxidative coupling of primary and secondary alcohols with phenylhydrazine: Synthesis of 1,3,5-trisubstituted pyrazoles DOI
Zohreh Najminejad, Davood Azarifar, Shohreh Khatami

et al.

Journal of Chemical Sciences, Journal Year: 2025, Volume and Issue: 137(1)

Published: Feb. 27, 2025

Language: Английский

Citations

0
Orthometallated Pd(ii) C^N^S pincer complex catalyzed sustainable synthesis of bis(indolyl)methanesviaacceptorless dehydrogenative coupling of alcohols DOI
Savarimuthu Selvan Clinton, Rengan Ramesh, J.G. Małecki

et al.

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(11), P. 3358 - 3365

Published: Jan. 1, 2023

New orthometallated Pd( ii ) C^N^S pincer catalyst-mediated sustainable and cost-effective synthesis of pharmacologically important bis(indolyl)methanes (23 examples up to 95% yield) via ADC is reported.

Language: Английский

Citations

9
Transition-Metal-Free Dehydrogenation of Benzyl Alcohol for C–C and C–N Bond Formation for the Synthesis of Pyrazolo[3,4-b]pyridine and Pyrazoline Derivatives DOI
Sesuraj Babiola Annes,

Karuppaiah Perumal,

Kalaiselvan Anandhakumar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6039 - 6057

Published: April 26, 2023

A series of cascade reactions that produce a range functionalized aromatic heterocyclic compounds with pyrazole/pyrazoline cores have been developed. The method relies on metal-free dehydrogenative process to in-situ benzaldehydes. produced benzaldehyde was then allowed react some other substances, including acetophenone, pyrazole amine, and phenylhydrazine. intermediate from these substrates underwent several chemical processes, electrocyclization, the aza-Diels-Alder reaction, formation intramolecular C-N bonds. These positive outcomes would open up possibility producing biologically active pyrazolo[3,4-b]pyridine pyrazoline derivatives through variety possible reactions.

Language: Английский

Citations

9