Isothiazoles

Clerici, Francesca; Gelmi, Maria Luisa; Pellegrino, Sara

doi:10.1016/b978-008044992-0.00405-3

Cited by 7 publications

(6 citation statements)

References 528 publications

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“…In the general context of the chemistry of heterocyclic compounds, data on the chemical properties of isothiazoles are presented in review articles, [28][29][30] whilst isothiazoles have been directly reviewed, [31][32][33][34] and covered in a monograph 35 devoted to biologically active isothiazoles. There are also reports summarizing data on isothiazole-ring-containing compounds in crop protection, 36 the involvement of the isothiazole core in cross-coupling reactions, 37 and [4+2] cycloadditions of isothiazole derivatives.…”

Section: Syn Thesismentioning

confidence: 99%

“…Finally, a very interesting and original example of (3+2)heterocyclization is the recently proposed method of asymmetric synthesis of condensed isothiazoles 32 through a copper-catalyzed direct asymmetric conjugate addition of allyl cyanide (33) to ,-unsaturated thioamides 34 (Scheme 16). 61…”

Section: Scheme 14 the Cycloaddition Reaction Between 2-oxo-134-oxamentioning

confidence: 99%

“…In some cases, interactions with nucleophilic and electrophilic reagents may lead to the ring-opening of the isothiazole. 33 The achievements in the development of methods for the functionalization of the isothiazole nucleus and advances in the transformation of the side chains of the heterocycle, without involving the heterocycle itself in the reaction, will be considered separately. Significant attention will be paid to the development of the chemistry of halogen-substituted isothiazoles, which are highly reactive synthetic blocks, allowing the ability to obtain polyfunctional isothiazoles with a wide variety of substituents.…”

Section: Review Syn Thesismentioning

confidence: 99%

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Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes

et al. 2019

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The chemistry of isothiazoles is being intensively developed, which is evidenced by the wide range of selective transformations involving the isothiazole heterocycle and the high biological activity of its derivatives that can be used as effective new drugs and plant protection chemicals. Some representatives of isothiazoles have proven to be synergists of bioactive substances, which opens the way to lower the doses of drugs used and is especially important in cancer chemotherapy. In the framework of the present review, the accomplishments in the chemistry of isothiazoles over the past 18 years are examined, whilst current strategies for the synthesis of isothiazole-containing molecules and key directions of studies in this field of heterocyclic chemistry are discussed. Considerable attention is paid to chlorinated isothiazoles and strategies for their use in the synthesis of biologically active substances. In addition, a comprehensive review of existing literature in the field of metal complexes of isothiazoles is given, including the results and prospects for the practical use of isothiazole–metal complexes as catalysts for cross-coupling reactions in aqueous and aqueous–alcoholic media (‘green chemistry’).1 Introduction2 Synthesis by Ring-Forming Reactions2.1 Intramolecular Cyclization2.2 (4+1)-Heterocyclization2.3 (3+2)-Heterocyclization2.4 Syntheses by Ring Transformations3 Isothiazoles by Ring Functionalization Reactions: Nucleophilic Substitution, Cross-Coupling and Side-Chain Functionalization4 Selected Syntheses of Biologically Active Isothiazole Derivatives5 Isothiazoles in the Synthesis of Transition-Metal Complexes and in Metal-Complex Catalysis6 Conclusion

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Section: Syn Thesismentioning

confidence: 99%

Section: Scheme 14 the Cycloaddition Reaction Between 2-oxo-134-oxamentioning

confidence: 99%

Section: Review Syn Thesismentioning

confidence: 99%

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Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes

et al. 2019

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“…Commercial isothiazoles include the Kathon preservatives, the artificial sweetener saccharin, and the antibacterial sulfa drug, sulfasomizole. The chemistry of isothiazoles has been reviewed . Most strategies for preparing isothiazoles involve construction of the isothiazole ring with the desired carbon substituents in place, as such the routes are often product specific …”

mentioning

confidence: 99%

“…The chemistry of isothiazoles has been reviewed. 4 Most strategies for preparing isothiazoles involve construction of the isothiazole ring with the desired carbon substituents in place, as such the routes are often product specific. 5 By combining modern transition metal-catalyzed C-C bond forming reactions with readily available halo-substituted isothiazole scaffolds, useful nonproduct specific routes to alkyl-, 6 alkenyl-, 7 alkynyl-, 7a,b,8 aryl-, 6,7b,9 and heteroaryl-substituted 6b,7b,9 isothiazoles can be realized.…”

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confidence: 99%

Silver-Mediated Palladium-Catalyzed Direct C−H Arylation of 3-Bromoisothiazole-4-carbonitrile

Ioannidou

Koutentis

2011

Org. Lett.

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Silver(I) fluoride-mediated Pd-catalyzed C-H direct arylation/heteroarylation of 3-bromoisothiazole-4-carbonitrile (1a) gives twenty-four 5-aryl/heteroaryl-3-bromoisothiazole-4-carbonitriles. The reaction was partially optimized with respect to catalyst, ligand, and base. During this study 3,3'-dibromo-5,5'-biisothiazole-4,4'-dicarbonitrile (3a) was isolated as a byproduct and subsequently prepared via the silver-mediated Pd-catalyzed oxidative dimerization of 3-bromoisothiazole-4-carbonitrile in 67% yield. The analogous phenylation and oxidative dimerization of 3-chloroisothiazole-4-carbonitrile (1b) gave 3-chloro-5-phenylisothiazole-4-carbonitrile (4) and 3,3'-dichloro-5,5'-biisothiazole-4,4'-dicarbonitrile (3b) in 96% and 69% yields, respectively.

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Divergent C−H Amidations and Imidations by Tuning Electrochemical Reaction Potentials

et al. 2022

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Electrochemical C−H functionalizations are attractive transformations, as they are capable of avoiding the use of transition metals, pre‐oxidized precursors, or suprastoichiometric amounts of terminal oxidants. Herein an electrochemically tunable method was developed that enabled the divergent formation of cyclic amines or imines by applying different reaction potentials. Detailed cyclic voltammetry analyses, coupled with chronopotentiometry experiments, were carried out to provide insight into the mechanism, while atom economy was assessed through a paired electrolysis. Selective C−H amidations and imidations were achieved to afford five‐ to seven‐membered sulfonamide motifs that could be employed for late‐stage modifications.

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Isothiazoles

Cited by 7 publications

References 528 publications

Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes

Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes

Silver-Mediated Palladium-Catalyzed Direct C−H Arylation of 3-Bromoisothiazole-4-carbonitrile

Divergent C−H Amidations and Imidations by Tuning Electrochemical Reaction Potentials

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