☆ 4.5 Article

Catalyst-Free, Heating-Induced Desulfurization Annulation of CF3-Imidoyl Sulfoxonium Ylides with Isothiocyanates for the Synthesis of 2-Trifluoromethyl-4-aminoquinolines

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Applied

Copper-Catalyzed Decarbonylative Cyclization of Isatins and Trifluoroacetimidohydrazides for the Synthesis of 2-(5-Trifluoromethyl-1,2,4-triazol-3-yl)anilines

Yu Zhang et al.

Summary: A copper-catalyzed intramolecular decarbonylative cyclization reaction of isatins and trifluoroacetimidohydrazides has been developed for the synthesis of 2-(5-trifluoromethyl-1,2,4-triazol-3-yl)aniline derivatives. This transformation involves a cascade condensation, hydrolysis, decarboxylation, and intramolecular C-N bond formation sequence. The resulting 1,2,4-triazole products with a free amino group can be easily converted into other useful compounds.

ADVANCED SYNTHESIS & CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Organic

Transition-Metal-, Additive-, and Solvent-Free [3+3] Annulation of RCF2-Imidoyl Sulfoxonium Ylides with Cyclopropenones to Give Multifunctionalized CF3-Pyridones

Si Wen et al.

Summary: An efficient strategy was developed to synthesize 1,3,4-triaryl-6-trifluoromethylpyridones in good yields from CF3-imidoyl sulfoxonium ylides and cyclopropenones. The reaction proceeded under transition-metal-, additive-, and solvent-free conditions, generating dimethyl sulfoxide as byproduct and tolerating various functional groups.

JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Rh(III)-Catalyzed Dual C-H Activation/Cascade Annulation of Benzimidates and CF3-Imidoyl Sulfoxonium Ylides for the Synthesis of Trifluoromethyl-Decorated Benzo[de][1,8]naphthyridines

Yu Zhang et al.

Summary: An efficient and straightforward approach for the synthesis of trifluoromethyl-decorated benzo[de][1,8]naphthyridines has been achieved via Rh(III)-catalyzed dual C-H activation and cascade annulation. The optoelectronic properties of the obtained fused aromatic products have also been investigated.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Ruthenium-Catalyzed Hydroxyl-Directed peri-Selective C-H Activation and Annulation of 1-Naphthols with CF3-Imidoyl Sulfoxonium Ylides for the Synthesis of 2-(Trifluoromethyl)-2,3-dihydrobenzo[de]chromen-2-amines

Zuguang Yang et al.

Summary: A novel ruthenium-catalyzed method using hydroxyl as a directing group has been developed for the selective C-H activation and annulation of 1-naphthols with CF3-substituted imidoyl sulfoxonium ylides. This strategy provides a facile and efficient route to diverse trifluoromethyl-containing 2,3-dihydrobenzo[de]chromen-2-amines, with notable advantages including readily available materials, excellent regioselectivity, good functional group compatibility, and scalability.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Formal [4+1] Annulation of Azoalkenes with CF3-Imidoyl Sulfoxonium Ylides and Dual Double Bond Isomerization Cascade: Synthesis of Trifluoromethyl-Containing Pyrazole Derivatives

Yue Sun et al.

Summary: A straightforward strategy for the metal-free construction of trifluoromethyl-containing pyrazole derivatives has been achieved. The protocol features mild conditions, easy operation, excellent substrate compatibility, and good regioselectivity. The utility of this method is demonstrated through scale-up reaction and further elaboration of the obtained pyrazole products.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-free synthesis of 3-trifluoromethyl-1,2,4-triazoles via oxidative cyclization of trifluoroacetimidohydrazides with N,N-dimethylformamide as carbon synthons

Shu-Ning Lu et al.

Summary: A metal-free approach for the synthesis of 3-trifluoromethyl-1,2,4-triazoles using DMF as the source of synthesis has been disclosed. The application potential of this method has been demonstrated in the synthesis of the key skeleton of factor IXa inhibitors.

GREEN SYNTHESIS AND CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

One-pot synthesis of 3-trifluoromethylbenzo[b][1,4]oxazines from CF3-imidoyl sulfoxonium ylides with 2-bromophenols

Mingshi Pan et al.

Summary: A method for accessing 3-trifluoromethyl-1,4-benzoxazines from CF3-imidoyl sulfoxonium ylides and 2-bromophenols has been demonstrated. This method proceeds through a one-pot two-step sequence involving O-H insertion and annulation, and offers the advantages of a broad substrate scope, excellent functional tolerance, and simplicity of operation.

CHEMICAL COMMUNICATIONS (2022)

添加到收藏夹

Article Chemistry, Organic

Ruthenium(ii)-catalyzed synthesis of CF3-isoquinolinones via C-H activation/annulation of benzoic acids and CF3-imidoyl sulfoxonium ylides

Si Wen et al.

Summary: The ruthenium(ii)-catalyzed C-H activation/annulation reaction of benzoic acids and CF3-imidoyl sulfoxonium ylides, enabled by weak O-coordination, has been achieved to synthesize a series of 3-trifluoromethylisoquinolinones in yields ranging from 37% to 75%.

ORGANIC CHEMISTRY FRONTIERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Controllable access to trifluoromethyl-containing indoles and indolines: palladium-catalyzed regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides

Hefei Yang et al.

Summary: A substrate-controlled regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides has been developed to synthesize structurally diverse trifluoromethyl-containing indoles and indolines. The regioselectivity of the reaction is determined by the structure of the alkene substrates.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Applied

Palladium-Catalyzed Carbonylative Synthesis of 2-(Trifluoromethyl)quinazolin-4(3H)-ones from Trifluoroacetimidoyl Chlorides and Nitro Compounds

Le-Cheng Wang et al.

Summary: A procedure for the palladium-catalyzed carbonylative reaction has been developed for the synthesis of pharmaceutically valuable 2-(trifluoromethyl)quinazolin-4(3H)-ones. The transformation uses Mo(CO)(6) as both a convenient CO source and a reducing reagent. This newly developed protocol is compatible with various nitro compounds and can be readily scaled up to a 1 mmol scale.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Organic

Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles

Si Wen et al.

Summary: A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction has been developed for the synthesis of 1,2,3-trisubstituted 5-trifluoromethylpyrroles from CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds, yielding products in 27-78% yield. The reaction exhibits a broad substrate scope and produces dimethyl sulfoxide and water as byproducts.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Palladium-catalyzed carbonylative synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and aryl iodides

Jianhua Tang et al.

Summary: A novel synthetic method for the preparation of pharmaceutically valuable 5-trifluoromethyl-1,2,4-triazoles has been achieved using a palladium-catalyzed three-component carbonylative reaction. The reaction conditions are mild, efficient, and have a broad substrate scope.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Article Chemistry, Organic

Copper-mediated [3+2] cycloaddition of trifluoroacetimidoyl chlorides and N-isocyanoiminotriphenylphosphorane for the synthesis of 3-trifluoromethyl-1,2,4-triazoles

Hefei Yang et al.

Summary: A simple and direct method for synthesizing 3-trifluoromethyl-1,2,4-triazoles via copper-mediated [3 + 2] cycloaddition of trifluoroacetimidoyl chlorides and N-isocyanoiminotriphenylphosphorane (NIITP) has been described. The use of Mo(CO)(6) as an effective promoter to activate NIITP allows for easily accessible reagents, mild reaction conditions, a wide substrate scope, high efficiency, and reproducibility on a 3 mmol scale.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Article Chemistry, Medicinal

Metabolic and Pharmaceutical Aspects of Fluorinated Compounds

Benjamin M. Johnson et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Organic

Silver-Catalyzed Cascade Cyclization Reaction of Isocyanides with Sulfoxonium Ylides: Synthesis of 3-Aminofurans and 4-Aminoquinolines

Yong-Xin Liang et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Review Chemistry, Organic

Trifluoroacetimidoyl halides: a potent synthetic origin

Zhengkai Chen et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

添加到收藏夹

Article Chemistry, Organic

Annulation Reactions of In-Situ-Generated N-(Het)aroyldiazenes with Isothiocyanates Leading to 2-Imino-1,3,4-oxadiazolines

Qiongli Zhao et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Medicinal

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design

Nicholas A. Meanwell

JOURNAL OF MEDICINAL CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Organic

Preparation of Trifluoromethylated (Arylaminomethylene)malononitriles Suitable for Synthesis of 4-Amino-2-(trifluoromethyl) quinoline Derivatives by Intramolecular Friedel-Crafts Reaction

Fariba Rahmani et al.

SYNTHESIS-STUTTGART (2018)

添加到收藏夹

Article Chemistry, Organic

Highly Efficient Construction of 2-Fluoroalkyl Quinolines through a Palladium-Catalyzed 6-endo-trig Heck Cyclization Reaction

Fangwai Han et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

添加到收藏夹

Review Chemistry, Medicinal

A review on anticancer potential of bioactive heterocycle quinoline

Obaid Afzal et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2015)

添加到收藏夹

Review Chemistry, Medicinal

Medicinal applications of perfluoroalkylated chain-containing compounds

Eva Prchalova et al.

FUTURE MEDICINAL CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible-Light-Induced Radical Cyclization of Trifluoroacetimidoyl Chlorides with Alkynes: Catalytic Synthesis of 2-Trifluoromethyl Quinolines

Xichang Dong et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

添加到收藏夹

Article Chemistry, Medicinal

Quinolines as Chemotherapeutic Agents for Leishmaniasis

Kristie A. Reynolds et al.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Organic

Cu-catalyzed tandem reactions of fluorinated alkynes with sulfonyl azides en route to 2-trifluoromethylquinolines

Yajun Li et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

添加到收藏夹

Article Biochemistry & Molecular Biology

Quinoline as a Privileged Scaffold in Cancer Drug Discovery

V. R. Solomon et al.

CURRENT MEDICINAL CHEMISTRY (2011)

添加到收藏夹

Article Chemistry, Applied

Efficient Synthesis of 2-Fluoromethylated Quinolines via Copper-Catalyzed Alkynylation and Cyclization of Fluorinated Imidoyl Iodides

Shan Li et al.

ADVANCED SYNTHESIS & CATALYSIS (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium catalyzed synthesis of 2-trifluoromethylquinolines through a domino Sonogashira-alkyne carbocyclization process

Zixian Chen et al.

CHEMICAL COMMUNICATIONS (2010)

添加到收藏夹

Review Chemistry, Medicinal

Quinolines and structurally related heterocycles as antimalarials

Kirandeep Kaur et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2010)

添加到收藏夹

Article Chemistry, Medicinal

Structure-Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating Mycobacterium tuberculosis

Annamaria Lilienkampf et al.

JOURNAL OF MEDICINAL CHEMISTRY (2009)

添加到收藏夹

Article Chemistry, Organic

Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines

Pravin R. Likhar et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2009)

添加到收藏夹

Editorial Material Chemistry, Medicinal

The many roles for fluorine in medicinal chemistry

William K. Hagmann

JOURNAL OF MEDICINAL CHEMISTRY (2008)

添加到收藏夹

Review Biochemistry & Molecular Biology

Quinoline, quinazoline and acridone alkaloids

Joseph P. Michael

NATURAL PRODUCT REPORTS (2008)

添加到收藏夹

Article Chemistry, Organic

Palladium-catalyzed chloroimination of imidoyl chlorides to a triple bond: An intramolecular reaction leading to 4-chloroquinolines

Akira Isobe et al.

ORGANIC LETTERS (2008)

添加到收藏夹

Review Multidisciplinary Sciences

Fluorine in pharmaceuticals:: Looking beyond intuition

Klaus Mueller et al.

SCIENCE (2007)

添加到收藏夹

Article Chemistry, Organic

A formal total synthesis of virantmycin:: A modular approach towards tetrahydroquinoline natural products

Daniel Keck et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2006)

添加到收藏夹

Article Pharmacology & Pharmacy

Pharmacology of N-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2-(trifluoromethyl)-5-quinoline carboxamide (SCH 351591), a novel, orally active phosphodiesterase 4 inhibitor

MM Billah et al.

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS (2002)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis and antibacterial evaluation of certain quinolone derivatives

YL Chen et al.

JOURNAL OF MEDICINAL CHEMISTRY (2001)

添加到收藏夹

Article Chemistry, Organic

Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines

H Amii et al.

ORGANIC LETTERS (2001)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.