4.7 Article

Ring-Opening-Recombination Strategy Based on 2-Methylbenzothiazole Salts: Syntheses of Thiazinopyrrole Fused-Ring Derivatives

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Site-Selective 1,4-Difunctionalization of Nitrogen Heteroaromatics for Constructing Vinylidene Heterocycles

Qianlin He et al.

Summary: A one-pot protocol was developed for constructing 1,4-difunctionalized quinoline/pyridine derivatives through the reaction of N-heteroaromatics, alkyl halides, and active methylene/methyl compounds. The transformation involves dearomative functionalization of an in situ-activated N-heteroaromatic to construct new C-N and C=C bonds, with broad substrate scope and functional group tolerance.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Facile preparation of dihydro-1,4-benzothiazine derivatives via oxidative ring-expansion of 2-aminobenzothiazoles with olefins

Qing Sun et al.

Summary: A concise and efficient method for the preparation of dihydro-1,4-benzothiazine derivatives via oxidative ring-expansion of 2-aminobenzothiazoles with olefins under metal-free conditions is described. The protocol demonstrates moderate-to-good yields and is applicable to a wide range of readily accessible 2-aminobenzothiazoles and olefins. The [4+2] heteroannulation between the intermediacy of oxidative ring-opening of 2-aminobenzothiazoles and olefins is suggested to rationalize the formation of the product.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

Cross-coupling of 2-methylquinolines and in-situ activated isoquinolines: Construction of 1,2-disubstituted isoquinolinones

Jianyi Shi et al.

Summary: In this study, a method for forming C(sp3)-C(sp2) bonds via copper catalyst-promoted cross coupling was developed. The reaction involved the sequential functionalization of the N1, C3, and C1 positions of 3-haloisoquinoline, resulting in the formation of new C-N, C=O, and C-C bonds. This method enables the efficient synthesis of 1,2-disubstituted isoquinolinones.

CHINESE CHEMICAL LETTERS (2022)

Review Biochemistry & Molecular Biology

Pyrazine and Phenazine Heterocycles: Platforms for Total Synthesis and Drug Discovery

Robert W. Huigens III et al.

Summary: This article reviews the biological activities and clinical applications of various pyrazine and phenazine compounds, discusses the related basic science knowledge and innovative synthetic methods, and highlights the potential of these heterocycles in medicine.

MOLECULES (2022)

Article Multidisciplinary Sciences

Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis

He Zhao et al.

Summary: The authors demonstrate a dearomative, diastereoselective annulation of azaarenes via ruthenium(II) reductive catalysis, showing excellent selectivity, mild conditions, and broad substrate and functional group compatibility, with the products formed via hydride transfer-initiated beta-aminomethylation and alpha-arylation of the pyridyl core.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

Divergent Synthesis of Fused Tetracyclic Heterocycles from Diarylalkynes Enabled by the Selective Insertion of Isocyanide

Meng Li et al.

Summary: Herein, a direct and efficient synthesis of diverse polysubstituted fused tetracyclic heterocycles with good functional group tolerance from diarylalkynes under different palladium catalytic systems is presented. The unprecedented intermolecular nucleopalladation of diarylalkynes through the highly selective sequential double insertion of isocyanide was achieved for the first time in this study. The practicality of this method was further demonstrated by the construction of various bioactive molecules and important structural motifs, with potential applications in materials science and biochemistry. In addition, density functional theory calculations revealed an interesting Pd walk during the cyclization process.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Nitrogen-Doped Carbon Supported Nanocobalt Catalyst for Hydrogen-Transfer Dearomative Coupling of Quinolinium Salts and Tetrahydroquinolines

Shengting Xu et al.

Summary: A nitrogen-doped carbon supported nanocobalt catalyst was developed and successfully utilized for the hydrogen transfer coupling of quinolinium salts and tetrahydroquinoline compounds, resulting in the synthesis of a series of 2-substituted N-alkyl-tetrahydroquinolines. This catalytic conversion method offers advantages such as excellent hydrogen transfer selectivity, a reusable and inexpensive catalyst, and environmental friendliness.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Facile Synthesis of 2-Methylenebenzothiazoles from Benzothiazole Salts and 4-Hydroxycoumarins by Ball Milling

Shengting Xu et al.

Summary: This study presents a simple and practical method for synthesizing 2-methylenebenzothiazoles via coupling reactions. The reaction proceeds under mechanochemical conditions without the need for catalysts or solvents, showing good substrate range and functional compatibility. The resulting 2-methylenebenzothiazoles exhibit strong luminescence and aggregation-induced emission (AIE) properties, indicating their potential as fluorescent materials.

CHEMISTRY-AN ASIAN JOURNAL (2022)

Article Multidisciplinary Sciences

Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes

Jin-Ping Wang et al.

Summary: The authors report a Pd-catalyzed migratory cycloannulation strategy for the efficient construction of a wide range of azahetereocycles. This finding is of great significance in drug discovery and synthetic chemistry.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Analytical

Oxygen sensing properties of thianthrene and phenothiazine derivatives exhibiting room temperature phosphorescence: Effect of substitution of phenothiazine moieties

Karolis Leitonas et al.

Summary: This study reports on four new derivatives of thianthrene and phenothiazine as emitters for oxygen sensing. It discusses the effects of the substitution pattern of phenothiazine moiety on various properties of the compounds. The compounds exhibited diverse photophysical properties under different conditions, with the highest oxygen sensitivity demonstrated by a methylphenothiazinyl-disubstituted thianthrene dispersed in poly(methyl methacrylate).

SENSORS AND ACTUATORS B-CHEMICAL (2021)

Article Chemistry, Multidisciplinary

Tandem Catalytic Indolization/Enantioconvergent Substitution of Alcohols by Borrowing Hydrogen to Access Tricyclic Indoles

Guoqiang Yang et al.

Summary: An efficient tandem catalysis method has been developed for the direct conversion of alcohol-containing alkynyl anilines to valuable chiral 2,3-fused tricyclic indoles. Highly diastereoselective transformations of the tricyclic indole products also provide efficient access to a diverse array of complex polycyclic indoline compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

A ring expansion strategy towards diverse azaheterocycles

Ruirui Li et al.

Summary: This study presents a novel ring expansion strategy involving the cross-dimerization of different strained rings through synergistic bimetallic catalysis, providing an efficient and scalable method for assembling diverse N-heterocycles. Preliminary mechanistic studies reveal that the C-C bond of strained ring ketones is cleaved by the Pd-0 species during the reaction.

NATURE CHEMISTRY (2021)

Article Chemistry, Organic

Mutasynthesis of Physostigmines in Myxococcus xanthus

Lea Winand et al.

Summary: By combining chemical synthesis with pathway refactoring, a series of physostigmine analogues with altered specificity and toxicity profiles were produced in the heterologous host. Among the compounds generated, the promising drug candidate phenserine was included, which was previously only accessible through total synthesis. This study provides a new approach for the development of novel therapeutics.

ORGANIC LETTERS (2021)

Article Chemistry, Applied

Synthesis of 1,4-Benzothiazines via KI/DMSO/O2-Mediated Three-Component Oxidative Cyclization/Coupling

Jinwu Zhao et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Multidisciplinary Sciences

Arene dearomatization through a catalytic N-centered radical cascade reaction

Rory C. McAtee et al.

NATURE COMMUNICATIONS (2020)

Article Multidisciplinary Sciences

Identification of phenothiazine derivatives as UHM-binding inhibitors of early spliceosome assembly

Pravin Kumar Ankush Jagtap et al.

NATURE COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Catalytic Regio- and Stereoselective Alkene Sulfenoamination for 1,4-Benzothiazine Synthesis

Nur-E. Alom et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Organic

NIR-emitting benzothiazolium cyanines with an enhanced stokes shift for mitochondria imaging in live cells

Chathura S. Abeywickrama et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Article Chemistry, Medicinal

6-Substituted 9-fluoroquino[3,2-b]benzo[1,4]thiazines display strong antiproliferative and antitumor properties

Malgorzata Jelen et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Medicinal

Synthesis and antimalarial activity of pyrazolo and pyrimido benzothiazine dioxide derivatives

Arthur Barazarte et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2009)