☆ 4.6 Article

Visible-light-induced C(sp3)-H thiocyanation of pyrazolin-5-ones: a practical synthesis of 4-thiocyanated 5-hydroxy-1H-pyrazoles

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Organic

Electrochemical monofluoroalkylation cyclization of N-arylacrylamides to construct monofluorinated 2-oxindoles

Yanxia Lv et al.

Summary: An electrochemical method for monofluoroalkylation cyclization of N-arylacrylamides to synthesize monofluorinated 2-oxindoles has been developed. This method utilizes dimethyl 2-fluoromalonate as a monofluoroalkyl radical precursor and eliminates the need for prefunctionalized monofluoroalkylation reagents and sacrificial oxidants. Various monofluorinated nitrogen-containing heterocyclic compounds were efficiently obtained with satisfactory yields from easily available materials.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Add to Collection

Article Chemistry, Organic

A Traceless Heterocyclic Amine Mediator in Regioselectivity-Switchable Formal [1+2+2] Cycloaddition Reaction to 1,3,4-and 1,4,5-Trisubstituted Pyrazoles

Jie Huo et al.

Summary: Switchable multicomponent reactions have been developed to construct compound libraries with diverse and complex skeletons by altering the reaction conditions. This study presents a regioselectivity-switchable formal [1 + 2 + 2] cycloaddition reaction using difluoroalkyl compounds, enaminones, and RNHNH2, with 1-methylindazol-3-amine as a traceless mediator. The reaction switches the inherent regioselectivity from 1,3,4-trisubstituted pyrazoles to 1,4,5-trisubstituted pyrazoles. Notable features include mild conditions, simple operation, and broad scopes.

ORGANIC LETTERS (2023)

Add to Collection

Article Chemistry, Organic

Organoelectrophotocatalytic C-H Silylation of Heteroarenes

Qinhui Wan et al.

Summary: An organoelectrophotocatalytic approach has been developed for the C-H silylation of heteroarenes through dehydrogenation cross-coupling with H2 evolution. The strategy uses 9,10-phenanthrenequinone as both an organocatalyst and a hydrogen atom transfer reagent, eliminating the need for external reagents. This approach shows excellent regioselectivity and can be applied to various heteroarenes with satisfactory yields.

ORGANIC LETTERS (2023)

Add to Collection

Article Chemistry, Organic

Paired electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol

Yanxia Lv et al.

Summary: A site-selective electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol through paired electrolysis is developed, where the anodic oxidation of Br- produced by the cathodic reduction of 2-bromoethan-1-ol is essential. The method shows good compatibility with common functional groups and can be easily scaled up. A variety of brominated products can be obtained with satisfactory yields at room temperature in a simple undivided cell.

ORGANIC CHEMISTRY FRONTIERS (2023)

Add to Collection

Article Chemistry, Inorganic & Nuclear

CuI-catalyzed sulfenylation of 1-aryl trifluoromethyl pyrazolones: Direct formation of C-S-C bond using aryl iodides and carbon disulfide

Vaibhav D. Prajapati et al.

Summary: A novel approach for synthesizing fluorinated sulfenyl pyrazolones was described using CuI catalyst, aryl iodides, and carbon disulfide, which is simple, efficient, and provides good yields.

JOURNAL OF FLUORINE CHEMISTRY (2022)

Add to Collection

Review Chemistry, Multidisciplinary

Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation

Pran Gopal Karmaker et al.

Summary: Techniques utilizing photo- and electrochemically induced reactions have been developed to accelerate organic processes. This review highlights significant advances in photo- and electrochemically driven thiocyanation reactions, focusing on different concept processes for thiocyanation bonds and emphasizing the synthetic and mechanistic characteristics of these reactions.

RSC ADVANCES (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Visible-light-induced novel cyclization of 2-(2-(arylethynyl)benzylidene)-malononitrile derivatives with 2,6-di(tert-butyl)-4-methylphenol to bridged spirocyclic compounds

Xiaofei Xie et al.

Summary: A green and highly efficient strategy was developed for the preparation of bridged spirocyclic compounds via visible-light-induced cyclization. The reaction proceeded smoothly under simple and mild conditions, yielding the desired products in good yields.

CHINESE CHEMICAL LETTERS (2022)

Add to Collection

Article Chemistry, Applied

Photoinduced Three-Component Cyclization of Arylamines, Enaminones and Difluorobromoacetates to 2,3-Difunctionalized Quinolines

Jie Huo et al.

Summary: A photoinduced multicomponent reaction involving arylamines, enaminones, and difluorobromoacetates has been developed for the synthesis of 2,3-difunctionalized quinolines. This strategy demonstrates broad functional group tolerance and wide substrate scopes, allowing for further synthetic applications of the resulting products. Mechanistic studies have revealed that intermolecular [3+3] cyclization between in-situ generated 1,3-vinylimine ions and arylamines is the crucial step in this transformation.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Organic

Photocatalytic C-H Thiocyanation of NH2-Enaminones and the Tunable Synthetic Routes to 2-Aminothiazoles and 2-Thiazolinones

Junlong Zeng et al.

Summary: Visible light photocatalytic reactions of NH2- enaminones and ammonium thiocyanate have been successfully used for the selective alpha-C-H thiocyanation, providing a sustainable synthesis route for thiocyanated NH2- enaminones. Furthermore, the resulting thiocyanated enaminone products can be readily transformed into 2-aminothiazoles and 2-thiazolinones through a simple operation.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1H)-ones with Acyloxy Nitroso Compounds

Runye Gao et al.

Summary: In this study, a photoinitiated radical relay reaction of quinoxalin-2(1H)-ones using acyloxy nitroso compounds as radical sources is described. The difunctionalization of quinoxalin-2(1H)-ones, involving the simultaneous construction of C-C and N-N bonds via radical relay reaction, is rarely reported. Furthermore, the obtained products undergo sequential reactions to access C7-NO2 of quinoxalin-2(1H)-ones under mild conditions.

ORGANIC LETTERS (2022)

Add to Collection

Review Chemistry, Organic

Recent progress of direct thiocyanation reactions

Haixin Chen et al.

Summary: Thiocyanates are commonly found in natural products, synthetic drugs, and bioactive molecules, and many thiocyanate derivatives have shown excellent antibacterial, antiparasitic, and anticancer activities. Thiocyanation is a simple and fast method to introduce SCN groups at target sites, constructing thiocyanates with broad application prospects.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions

Zhihui Wang et al.

Summary: A practical synthesis method of alpha-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed, achieving high yields without additional photocatalysts under sunlight irradiation.

CHINESE CHEMICAL LETTERS (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Design and Use of Electrophilic Thiocyanating and Selenocyanating Reagents: An Interesting Trend for the Construction of SCN- and SeCN-Containing Compounds

Melissa Gao et al.

Summary: Organothiocyanate and organoselenocyanate compounds are important in organic chemistry as key intermediates for accessing sulfur- and selenium-containing compounds. Recent research has focused on original methodologies using electrophilic reagents to synthesize SCN- and SeCN-containing molecules. This review highlights the design of electrophilic sources and their applications in thiocyanation and selenocyanation of various compound classes.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Add to Collection

Article Chemistry, Organic

Visible-Light-Driven Multicomponent Cyclization by Trapping a 1,3-Vinylimine Ion Intermediate: A Direct Approach to Pyrimido[1,2-b]indazole Derivatives

Xiao Geng et al.

Summary: This study introduces a novel visible-light-driven three-component cyclization to synthesize pyrimido[1,2-b]indazole derivatives, allowing for the introduction of aliphatic substituents and good compatibility with complex bioactive molecules. It represents the first example of a photoinduced multicomponent reaction using bromodifluoroacetic acid derivatives as a C1-synthon.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Organic

Visible-Light-Mediated Additive-Free Decarboxylative Ketonization Reaction of Acrylic Acids: An Access to α-Thiocyanate Ketones

Zhi-Lv Wang et al.

Summary: This reaction utilizes visible light, inexpensive organic dye, and dioxygen to efficiently synthesize α-thiocyanate ketones from acrylic acids and ammonium thiocyanate. It is a green and convenient method with easy-to-obtain starting materials and products, showing potential applications in organic and pharmaceutical chemistry.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Photocatalytic C-H Thiocyanation of Corroles: Development of Near-Infrared (NIR)-Emissive Dyes

Kasturi Sahu et al.

Summary: A new method utilizing an in situ generated SCN radical to activate corrole macrocycles at room temperature has been developed, leading to the synthesis of tetrathiocyanatocorroles with altered photophysical properties reminiscent of chlorophyll-a. These newly synthesized molecules have potential applications as pigments in solar cells and NIR-emissive dyes, suggesting significant implications in C-H activation reactions through weak interactions.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Visible light-induced recyclable g-C3N4 catalyzed thiocyanation of C(sp2)-H bonds in sustainable solvents

Fan-Lin Zeng et al.

Summary: A metal-free photocatalytic strategy using carbon nitride as a catalyst has been developed for the preparation of thiocyanated heterocycles from inexpensive NH4SCN. Various thiocyanated heterocycles were successfully synthesized in good yields under green conditions, and the recyclable catalyst showed no significant loss of activities after multiple uses.

GREEN CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Visible-light-induced metal-free cascade cyclization of N-arylpropiolamides to 3-phosphorylated, trifluoromethylated and thiocyanated azaspiro[4.5]trienones

Fan-Lin Zeng et al.

Summary: A novel method using photocatalytic strategies to synthesize 3-phosphoryl/trifluoromethyl/thiocyanato azaspiro[4.5]trienones has been developed, utilizing 4CzIPN as a photocatalyst, with operational simplicity, scalability, metal-free conditions, wide reaction scope, and good functional group tolerance.

ORGANIC CHEMISTRY FRONTIERS (2021)

Add to Collection

Review Chemistry, Medicinal

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Zefeng Zhao et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2020)

Add to Collection

Article Chemistry, Organic

Metal-Free Direct C-H Thiolation and Thiocyanation of Pyrazolones

Tanakorn Kittikool et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Organic

Lewis Base/Bronsted Acid Cocatalysis for Thiocyanation of Amides and Thioamides

Qumruddeen et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Organic

Temperature-Controlled Chalcogenation and Chalcogenocyanation of Imidazopyridines in Water under Transition Metal-Free Conditions

Yu-Shen Zhu et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Pd-Catalyzed Directed Thiocyanation Reaction by C-H Bond Activation

Melissa Gao et al.

CHEMISTRY-A EUROPEAN JOURNAL (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, Applied

Potassium Persulfate-Mediated Thiocyanation of 2H-Indazole under Iron-Catalysis

Amrita Dey et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Dual Photoredox/Copper Catalysis for the Remote C(sp3)-H Functionalization of Alcohols and Alkyl Halides by N-Alkoxypyridinium Salts

Xu Bao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Article Chemistry, Organic

Palladium-Catalyzed Site-Selective sp(3) C-H Bond Thiocyanation of 2-Aminofurans

Yongtao Chen et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection

Article Chemistry, Organic

DABCO-catalyzed silver-promoted direct thiolation of pyrazolones with diaryl disulfides

Akkharaphong Thupyai et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Visible-light-promoted aerobic metal-free aminothiocyanation of activated ketones

Pan-Feng Yuan et al.

GREEN CHEMISTRY (2018)

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

Article Chemistry, Applied

Direct construction of sulfenylated pyrazoles catalyzed by I2 at room temperature

Shuang-Hong Hao et al.

CHINESE JOURNAL OF CATALYSIS (2017)

Add to Collection

Review Chemistry, Organic

Recent Advances in the C(sp2)-S Bond Formation Reactions by Transition Metal-Free C(sp2)-H Functionalization

Yunyun Liu et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2017)

Add to Collection

Review Chemistry, Multidisciplinary

Recent advances in the chemistry of organic thiocyanates

Thomas Castanheiro et al.

CHEMICAL SOCIETY REVIEWS (2016)

Add to Collection

Article Chemistry, Organic

Transition-Metal-Free Tandem Radical Thiocyanooxygenation of Olefinic Amides: A New Route to SCN-Containing Heterocycles

Hua Yang et al.

ORGANIC LETTERS (2015)

Add to Collection

Article Chemistry, Organic

Sulfenyiation of β-Diketones Using C-H Functionalization Strategy

Begur Vasanthkumar Varun et al.

ORGANIC LETTERS (2015)

Add to Collection

Article Chemistry, Organic

Visible-light-induced direct α-C(sp3)-H thiocyanation of tertiary amines

Arvind K. Yadav et al.

TETRAHEDRON LETTERS (2015)

Add to Collection

Article Chemistry, Organic

A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles

Weigang Fan et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Add to Collection

Article Chemistry, Inorganic & Nuclear

THE SYNTHESIS AND BIOLOGICAL ACTIVITIES OF [5-(4-SUBSTITUTED PHENYLSULFINYL/SULFONYL)-1,3-DIMETHYL-1H-PYRAZOL-4-YL]-ARYLMETHANONES

Bao-Lei Wang et al.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS (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

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

Irina P. Beletskaya et al.

CHEMICAL REVIEWS (2011)

Add to Collection

Article Chemistry, Medicinal

5-Cyclic Amine-3-arylsulfonylindazoles as Novel 5-HT6 Receptor Antagonists

Simon N. Haydar et al.

JOURNAL OF MEDICINAL CHEMISTRY (2010)

Add to Collection

Review Cardiac & Cardiovascular Systems

The novel antioxidant edaravone: From bench to bedside

Toshiaki Watanabe et al.

CARDIOVASCULAR THERAPEUTICS (2008)

Add to Collection

Article Chemistry, Medicinal

Development of orally bioavailable bicyclic pyrazolones as inhibitors of tumor necrosis factor-α production

MP Clark et al.

JOURNAL OF MEDICINAL CHEMISTRY (2004)

Add to Collection

Article Chemistry, Medicinal

Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents

SAF Rostom et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2003)

Add to Collection

© Peeref 2019-2024. All rights reserved.