☆ 4.6 Article

Facile construction of C,N-disulfonated 5-amino pyrazoles through an iodine-catalyzed cascade reaction

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

External electrolyte-free electrochemical one-pot cascade synthesis of 4-thiocyanato-1 H-pyrazoles

Wei-Bao He et al.

Summary: A practical method for the synthesis of 4-thiocyanato-1H-pyrazoles was established through an electrochemical cascade reaction of hydrazines, 1,3-diones and NH4SCN under metal-, chemical oxidant- and external electrolyte-free conditions. Importantly, both a gram-scale synthesis of 4-thiocyanato-1H-pyrazoles and five one-pot sequential transformations starting from hydrazine were successfully achieved.

CHINESE CHEMICAL LETTERS (2023)

Add to Collection

Article Chemistry, Applied

Iodine-Catalyzed Double [4+2] Oxidative Annulations for the Synthesis of Bipyrazines from Ketones and Diamines by a Domino Strategy

Yuxin Ding et al.

Summary: An iodine-catalyzed double [4+2] oxidative annulation of ketones and diamines is reported, leading to the synthesis of substituted dimeric pyrazines under metal-free conditions through a multi-pathway coupled domino strategy. During this process, one C-C and four C-N bonds are formed from two ketones and two diamines.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Applied

A Synthetic Protocol for the Construction of Chroman-Spiroquinazolin(thi)one Framework via a Metal-Free, Three-Component, Domino, Double Annulations

Lingfeng Wang et al.

Summary: A three-component domino approach for the synthesis of chroman-spiroquinazolin(thi)ones is described, which involves a condensation reaction followed by a hetero-Diels-Alder annulation. The reaction shows broad substrate scope and can be conducted under metal-free catalytic conditions.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

A radical-radical cross-coupling reaction of xanthene with sulfonyl hydrazides: facile access to xanthen-9-sulfone derivatives

Sumit Das et al.

Summary: This study establishes a straightforward strategy for the direct incorporation of sulfonyl units into a xanthene moiety, yielding xanthen-9-sulfone derivatives in good to excellent yields via metal-free radical-radical cross-coupling reaction. The methodology uses easily accessible starting materials and proceeds efficiently under simple reaction conditions with a high degree of functional group compatibility.

CHEMICAL COMMUNICATIONS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

HFIP-catalyzed highly diastereoselective formal [4+2] cyclization to synthesize difluorinated multisubstituted chromans using difluoroenoxysilanes as C2 synthons

Jinshan Li et al.

Summary: This study developed a hexafluoroisopropanol-catalyzed highly diastereoselective formal [4 + 2] cyclization reaction. By employing difluoroenoxysilane as a new C2 synthon, this tandem protocol provides a simple and straightforward approach to assemble multiply functionalized difluorinated chromans with high to excellent diastereoselectivity.

CHINESE CHEMICAL LETTERS (2022)

Add to Collection

Article Chemistry, Organic

One-Pot Two-Step Strategy for Efficient Synthesis of 3-Aryl-4-(arylthio)-1H-pyrazol-5-amines Derivatives

Feng Yijiao et al.

Summary: In this study, a one-pot two-step reaction was established to efficiently construct 3-aryl-4-(arylthio)-1H-pyrazol-5-amines. The method offers high product yields and broad substrate applicability by simplifying the reaction steps.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Synthesis of Difluoromethylated Pyrazoles by the [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides

Tongyu Han et al.

Summary: The synthesis of novel difluoroacetohydrazonoyl bromides as difluoromethyl building blocks shows great potential for constructing difluoromethyl organic compounds. Their regioselective [3 + 2] cycloaddition reactions with ynones, alkynoates, and ynamides provide an efficient protocol for accessing difluoromethyl-substituted pyrazoles in good to excellent yields.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Substrate-Switched Chemodivergent Pyrazole and Pyrazoline Synthesis: [3+2] Cycloaddition/Ring-Opening Rearrangement Reaction of Azadienes with Nitrile Imines

Liang Tu et al.

Summary: A fundamentally new reaction model of benzofuran-derived azadienes (BDAs) has led to the synthesis of biologically important pyrazoles through a tandem [3 + 2] cycloaddition/ring-opening rearrangement reaction with nitrile imines. The nature and type of substrates determine two distinct reaction pathways, and minor modifications to the substrates allow access to spiro-pyrazolines.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Copper-Catalyzed Hydroamination of Oxa- and Azabenzonorbornadienes with Pyrazoles

Kundo Kim et al.

Summary: An efficient and highly chemo- and stereoselective copper-catalyzed hydroamination of oxa- and azabenzonorbornadienes with various pyrazole derivatives is described. The catalytic process is promoted by N-heterocyclic carbene ligands and KOt-Bu, allowing for the direct synthesis of new and versatile functionalized oxa(aza)benzonorbornyl pyrazoles starting from readily available oxa(aza)bicyclic alkenes. The synthetic utility of this method is demonstrated by transforming the obtained products into pyrazolyl-substituted naphthalenes.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

DMSO as a C1 Source for [2+2+1] Pyrazole Ring Construction via Metal-Free Annulation with Enaminones and Hydrazines

Haijin Guo et al.

Summary: The synthesis of 1,4-disubstituted pyrazoles was successfully achieved through a cascade reaction between enaminones, hydrazines, and DMSO catalyzed by molecular iodine in the presence of Selectfluor. DMSO played a dual role as the C-1 source and the reaction medium, and the synthesis of 1,3,4-trisubstituted pyrazoles using aldehydes as alternative C-1 building blocks was also accomplished.

ORGANIC LETTERS (2022)

Add to Collection

Review Chemistry, Physical

Desulfonylative Transformations of Sulfones by Transition-Metal Catalysis, Photocatalysis, and Organocatalysis

Masakazu Nambo et al.

Summary: This Review summarizes the recent advances in the desulfonylative transformations of sulfones using molecular catalysis. Different types of catalysts, including transition-metal catalysts, photocatalysts, and organocatalysts, are discussed. The design of the sulfonyl group is identified as a critical factor in controlling reactivity.

ACS CATALYSIS (2022)

Add to Collection

Article Chemistry, Physical

Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N-S Bond Activation of Sulfonamides

Jingsong Zhen et al.

Summary: A visible-light-mediated late-stage arylation of N-S bonds in sulfonamides has been developed using readily available imines as sulfonyl radical source. This methodology characterized by broad substrate scope and simple reaction conditions also has high atom economy.

ACS CATALYSIS (2022)

Add to Collection

Article Chemistry, Organic

Visible-light mediated cross-coupling of aryl halides with sodium sulfinates via carbonyl-photoredox/nickel dual catalysis

Shan Jiang et al.

Summary: A photoinduced nickel-catalyzed cross-coupling reaction of arylsulfinates with (hetero)aryl halides has been achieved using visible light. The reaction showed a broad substrate scope and good functional group tolerance, providing diarylsulfones in moderate to excellent yields. The mechanism involves oxidative addition, single-electron oxidation, reductive elimination, and electron transfer.

ORGANIC CHEMISTRY FRONTIERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones

Myunggi Jung et al.

Summary: Here, we report a convenient and general one-pot method for the synthesis of 1-sulfonylbicyclo[1.1.0]butanes via the dialkylmagnesium-mediated formation of 3-sulfonylcyclobutanol intermediates. This method was also extended to the synthesis of 1-sulfonylbicyclo[2.1.0]pentane (housane) analogues. Both procedures showed similar efficiency in gram-scale applications and demonstrated full stereospecificity when enantiopure epoxides were used, providing streamlined access to highly valuable optically active strain-release reagents.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Carbene-Catalyzed Enantioselective Sulfonylation of Enone Aryl Aldehydes: A New Mode of Breslow Intermediate Oxidation

Rui Deng et al.

Summary: A novel carbene-catalyzed sulfonylation reaction between enone aryl aldehydes and sulfonyl chlorides has been disclosed, leading to the efficient installation of sulfone moieties. The NHC catalyst provides activation and stereoselectivity control on a very remote site of the enone aryl aldehyde substrates. Water plays a crucial role in modulating catalyst deactivation and reactivation routes involving reactions between NHC and sulfonyl chloride.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Organic

Visible-light mediated cross-coupling of aryl halides with sodium sulfinates via carbonyl-photoredox/nickel dual catalysis

Shan Jiang et al.

Summary: In this study, a photoinduced nickel-catalyzed cross-coupling reaction was achieved with moderate to excellent yields of arylsulfinates and (hetero)aryl halides. The reaction demonstrated a broad substrate scope and good functional group tolerance, leading to the formation of diarylsulfones. The mechanism involved several steps, including oxidative addition, oxidation, reductive elimination, and release of the product. The photoredox and nickel catalytic cycles interacted through electron transfer.

ORGANIC CHEMISTRY FRONTIERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Visible-light-induced photoredox-catalyzed synthesis of benzimidazo [2,1-a]iso-quinoline-6(5H)-ones

Bin Wang et al.

Summary: A simple and efficient visible-light-induced photoredox-catalyzed diarylation of N-methacryloyl-2-arylbenzoimidazoles with aryl diazonium salts was developed in this study. The reaction provides a convenient access to a variety of benzimidazoisoquinolinones through the construction of two C-C bonds in one step under mild reaction conditions. The research was published by Elsevier B.V. and all rights are reserved.

CHINESE CHEMICAL LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Tris(pentafluorophenyl)borane-Catalyzed Carbenium Ion Generation and Autocatalytic Pyrazole Synthesis-A Computational and Experimental Study

Ayan Dasgupta et al.

Summary: The study focuses on metal-free organic synthesis using triarylboranes as catalysts for the selective synthesis of N-substituted pyrazoles through the generation of carbenium species. DFT studies reveal that the in situ generation of a carbenium species serves as an autocatalyst to prompt the regiospecific formation of N-substituted pyrazoles in good to excellent yields (up to 81 %).

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Medicinal

Discovery of Benzocyclic Sulfone Derivatives as Potent CXCR2 Antagonists for Cancer Immunotherapy

Yi Dong et al.

Summary: The study designed benzocyclic sulfone derivatives as potent CXCR2 antagonists, with lead compounds 9b and 11h showing high inhibitory effects on tumor growth in the Pan02 mouse model through oral administration. They also reduced neutrophils and MDSCs infiltration while enhancing CD3(+) T lymphocytes infiltration into tumor tissues.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Metal- and Solvent-Free Cascade Reaction for the Synthesis of Amino Pyrazole Thioether Derivatives

Sesuraj Babiola Annes et al.

Summary: The study developed an iodine-mediated cascade strategy to synthesize amino pyrazole thioether derivatives without the use of metals or solvents. The approach showed high selectivity in providing the compounds, avoiding the formation of undesired byproducts, and demonstrated the reactivity of nine sulfenylation sources. Overall, the iodine-mediated multicomponent reaction was shown to be more economically feasible, efficient, and environmentally friendly.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides

Marc Magre et al.

Summary: A bi-catalyzed synthesis of sulfonyl fluorides from (hetero)aryl boronic acids is demonstrated using organobismuth(III) catalysts, resulting in excellent yields and wide functional group tolerance. The catalytic cycle involves various organometallic steps without changing the oxidation state, forming a structurally unique bismuth sulfinate complex.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Article Chemistry, Medicinal

Development of Fluorescence Imaging Probes for Labeling COX-1 in Live Ovarian Cancer Cells

Jatinder Kaur et al.

Summary: Recent studies have shown an abnormal overexpression of cyclooxygenase-1 (COX-1) in various cancers, leading to the development of COX-1-selective inhibitors as potential anticancer drugs and imaging agents. Compound 17 exhibited favorable COX-1 inhibition and selectivity, making it a lead structure for developing a novel COX-1-selective fluorescent probe. The fluorescent probe, synthesized via click chemistry, was successfully used for targeting and visualizing COX-1 in living cells, specifically in ovarian cancer cell line OVCAR-3.

ACS MEDICINAL CHEMISTRY LETTERS (2021)

Add to Collection

Article Chemistry, Organic

Transition Metal-Free De Novo Synthesis of Sulfonated Pyrazoles from Sulfonyl Hydrazides, 1,3-Diketones, and Sodium Sulfinates at Room Temperature

Jiawen Chen et al.

Summary: A transition metal-free method has been established for the de novo construction of diverse sulfonated pyrazoles from commonly available sulfonyl hydrazides, 1,3-diketones, and sodium sulfinates under mild conditions. This method allows for the preparation of pyrazoles bearing two different sulfonyl groups in one step, with a diversity of substituents and a remarkably simple work-up process.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Converting molecular luminescence to ultralong room-temperature phosphorescence via the excited state modulation of sulfone-containing heteroaromatics

Zetong Ma et al.

Summary: By manipulating the molecular orbital properties of excited states and relaxation processes, the emission behaviors of luminophores can be greatly altered. For example, by facile substituent effect on a rigid benzothiazino phenothiazine tetraoxide (BTPO) core, luminescence conversion from thermally activated delayed fluorescence (TADF) to ultralong room-temperature phosphorescence (URTP) can be achieved. Dispersed in a polymer matrix, the BTPO derivatives exhibit a persistent bright green afterglow with long lifetimes of up to 822 ms and decent quantum yields of up to 11.6%.

CHEMICAL SCIENCE (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Electrochemical multicomponent synthesis of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions

Yan Wu et al.

Summary: An electrochemical multicomponent reaction was developed for the construction of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions, providing a green and straightforward protocol. A variety of 4-selanylpyrazole derivatives were synthesized from readily available raw materials with good to excellent yields.

GREEN CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides

Yueting Wei et al.

Summary: A new three-component reaction has been developed for the synthesis of 3-aryl-4-(arylthio)-1H-pyrazol-5-amines, with the use of NIS to facilitate sequential cyclization and sulfenylation reactions. The protocol demonstrates broad substrate scope, good functional group tolerance, and mild reaction conditions. Gram-scale synthesis and diverse transformations of the products further highlight the utility of this procedure.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C-H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones

Manman Sun et al.

SYNTHESIS-STUTTGART (2020)

Add to Collection

Article Chemistry, Physical

Transition Metal-free C-H Sulfonylation and Pyrazole Annulation Cascade for the Synthesis of 4-Sulfonyl Pyrazoles

Lihong Tian et al.

CHEMCATCHEM (2020)

Add to Collection

Article Chemistry, Organic

K2S2O8-promoted direct thiocyanation of pyrazolin-5-ones with ammonium thiocyanate at room temperature

Xiaokang Mao et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

Add to Collection

Article Chemistry, Multidisciplinary

V2O5/SiO2 AS AN EFFICIENT CATALYST IN THE SYNTHESIS OF 5-AMINO-PYRAZOLE DERIVATIVES UNDER SOLVENT FREE CONDITION

Tamer K. Khatab et al.

BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA (2019)

Add to Collection

Article Chemistry, Organic

Domino C-H Sulfonylation and Pyrazole Annulation for Fully Substituted Pyrazole Synthesis in Water Using Hydrophilic Enaminones

Yanhui Guo et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Add to Collection

Article Chemistry, Organic

Copper-Catalyzed Aminoboration from Hydrazones To Generate Borylated Pyrazoles

Kim N. Tu et al.

ORGANIC LETTERS (2019)

Add to Collection

Article Chemistry, Organic

In Situ Generation of Nitrilimines from Aryldiazonium Salts and Diazo Esters: Synthesis of Fully Substituted Pyrazoles under Room Temperature

Ying Shao et al.

ORGANIC LETTERS (2018)

Add to Collection

Review Chemistry, Medicinal

Recent advances of pyrazole-containing derivatives as anti-tubercular agents

Zhi Xu et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2017)

Add to Collection

Review Chemistry, Multidisciplinary

Review: biologically active pyrazole derivatives

Anam Ansari et al.

NEW JOURNAL OF CHEMISTRY (2017)

Add to Collection

Article Chemistry, Organic

Copper-Mediated Domino Cyclization/Trifluoromethylation/Deprotection with TMSCF3: Synthesis of 4-(Trifluoromethyl)pyrazoles

Quande Wang et al.

ORGANIC LETTERS (2017)

Add to Collection

Article Chemistry, Organic

Metal-free molecular iodine-catalyzed direct sulfonylation of pyrazolones with sodium sulfinates leading to sulfonated pyrazoles at room temperature

Wei Wei et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Add to Collection

Review Biochemistry & Molecular Biology

Recently reported biological activities of pyrazole compounds

Jessica Venancia Faria et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2017)

Add to Collection

Review Chemistry, Medicinal

The therapeutic voyage of pyrazole and its analogs: A review

Mohemmed Faraz Khan et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2016)

Add to Collection

Article Chemistry, Applied

Metal-Free Direct Construction of Sulfonamides via Iodine-Mediated Coupling Reaction of Sodium Sulfinates and Amines at Room Temperature

Wei Wei et al.

ADVANCED SYNTHESIS & CATALYSIS (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Direct synthesis of pyrazoles from esters using tert-butoxide-assisted C-(C=O) coupling

Bo Ram Kim et al.

CHEMICAL COMMUNICATIONS (2015)

Add to Collection

Review Chemistry, Medicinal

Recent advances in bioactive pyrazoles

S. Guniz Kucukguzel et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature

Kai Yang et al.

GREEN CHEMISTRY (2015)

Add to Collection

Article Chemistry, Organic

Metal-Free Iodine-Catalyzed Synthesis of Fully Substituted Pyrazoles and Its Sulphenylation

Jun Sun et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Copper-mediated pyrazole synthesis from 2,3-allenoates or 2-alkynoates, amines and nitriles

Bo Chen et al.

CHEMICAL COMMUNICATIONS (2014)

Add to Collection

Article Chemistry, Organic

Regioselective C2 Sulfonylation of Indoles Mediated by Molecular Iodine

Praewpan Katrun et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Add to Collection

Article Chemistry, Organic

Dual Roles of Sulfonyl Hydrazides: A Three-Component Reaction To Construct Fully Substituted Pyrazoles Using TBAI/TBHP

Jie Zhang et al.

ORGANIC LETTERS (2014)

Add to Collection

Article Chemistry, Organic

Lewis Base Catalyzed Synthesis of Multisubstituted 4-Sulfonyl-1H-Pyrazole Involving a Novel 1,3-Sulfonyl Shift

Yu Zhu et al.

ORGANIC LETTERS (2013)

Add to Collection

Article Chemistry, Medicinal

Pyrazoles as Promising Scaffold for the Synthesis of Anti-Inflammatory and/or Antimicrobial Agent: A Review

Adnan A. Bekhit et al.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2012)

Add to Collection

Article Chemistry, Organic

One-Pot, Two-Step Conversion of Aldehydes to Phosphonyl- and Sulfonylpyrazoles Using Bestmann-Ohira Reagent

Rahul Kumar et al.

ORGANIC LETTERS (2012)

Add to Collection

Article Chemistry, Organic

Regioselective Synthesis of Sulfonylpyrazoles via Base Mediated Reaction of Diazosulfones with Nitroalkenes and a Facile Entry into Withasomnine

Rahul Kumar et al.

ORGANIC LETTERS (2011)

Add to Collection

Article Chemistry, Multidisciplinary

Efficient Synthesis of Pyrazoles: Oxidative C-C/N-N Bond-Formation Cascade

Julia J. Neumann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Add to Collection

Article Chemistry, Organic

Design and Synthesis of Benzosultine-sulfone as a o-Xylylene Precursor via Cross-enyne Metathesis and Rongalite: Further Expansion to Polycyclics via Regioselective Diels-Alder Reaction

Sambasivarao Kotha et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

Add to Collection

Article Chemistry, Medicinal

Development of peptidomimetics with a vinyl sulfone warhead as irreversible falcipain-2 inhibitors

Roberta Ettari et al.

JOURNAL OF MEDICINAL CHEMISTRY (2008)

Add to Collection

Review Chemistry, Organic

1,3-dipolar cycloadditions of acetylenic sulfones in solution and on solid supports

Detian Gao et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

Add to Collection

Review Biochemistry & Molecular Biology

A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms

Claus Jacob

NATURAL PRODUCT REPORTS (2006)

Add to Collection

Review Food Science & Technology

Anticarcinagenic properties of garlic: A review

F Khanum et al.

CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION (2004)

Add to Collection

© Peeref 2019-2024. All rights reserved.