A Mild and Efficient Synthesis of 3-Aminosubstituted Isothiazole S-Oxides and their 5-Sulfanylsubstituted Derivatives

Casoni, Alessandro; Clerici, Francesca; Contini, Alessandro; Pellegrino, Sara; Sala, Alessandro

doi:10.2174/157017808786857534

Cited by 5 publications

(2 citation statements)

References 11 publications

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“…69 A mild approach to synthesize 3-amino-substituted isothiazole sulfoxides 50 through oxidation of the corresponding 3-aminoisothiazoles 51 with arylsulfonyloxaziridines 52 has been reported (Scheme 24). 70 Only minor amounts of dioxides 53 were formed under the described conditions. The reactivity of the resulting isothiazole sulfoxides toward sulfur nucleophiles has been studied and resulted in the formation of 5-sulfanyl-substituted 4,5-dihydroisothiazoles.…”

Section: Scheme 23 Oxidative Alkenylation Of the Isothiazole Ringmentioning

confidence: 86%

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: Scheme 23 Oxidative Alkenylation Of the Isothiazole Ringmentioning

confidence: 86%

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

et al. 2019

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“…Introduction. -Recently, we described the synthesis of chiral racemic isothiazolamine S-oxides A, starting from the corresponding isothiazolamines 1, and some preliminary studies on their reactivity toward S-nucleophiles which demonstrated the ability of the sulfoxide moiety to direct the addition affording the corresponding 5-(aryl-and alkylthio) derivatives in a fully diastereoselective way (Scheme 1) [1]. The availability of these new S-oxides A prompted us to continue our research on their reactivity.…”

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confidence: 99%

Fused Isothiazole S‐Oxide Systems from Cycloaddition Reactions of N‐Benzylisothiazol‐3‐amine 1‐Oxide

Clerici¹,

Casoni²,

Contini³

et al. 2009

Helvetica Chimica Acta

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The racemic N-benzylisothiazol-3-amine 1-oxide (2) was demonstrated to be an efficient partner in Diels -Alder reactions (Schemes 2 -4) and a good dipolarophile in 1,3-dipolar cycloaddition reactions with nitrile oxides (Scheme 5). Polycyclic isothiazole S-oxides with different substitution patterns were obtained from 2 in good yield and in a fully regioselective way. Improved diastereoselection was observed performing the Diels -Alder or 1,3-dipolar cycloaddition reactions in H 2 O.Introduction. -Recently, we described the synthesis of chiral racemic isothiazolamine S-oxides A, starting from the corresponding isothiazolamines 1, and some preliminary studies on their reactivity toward S-nucleophiles which demonstrated the ability of the sulfoxide moiety to direct the addition affording the corresponding 5-(aryl-and alkylthio) derivatives in a fully diastereoselective way (Scheme 1) [1]. The availability of these new S-oxides A prompted us to continue our research on their reactivity. In particular, we concentrated our attention on the aptitude of this system to act as an effective reaction partner in cycloaddition reactions which would allow the preparation of fused isothiazole S-oxide derivatives of both chemical and pharmacological interest. In fact, cycloaddition reactions appeared to be a very versatile tool to obtain new classes of isothiazoles or fused isothiazole systems or new or known heterocycles by the transformation of the primary cycloadducts similarly to the transformations described for the corresponding S,S-dioxides [2 -6]. The exploitation of the sulfoxide system could be considered of large interest due to the significant stereodifferentiating ability of the sulfinyl function [7]. Moreover, taking into account the general interest in environmental contamination, efforts were devoted in this work to develop cycloaddition processes with reduced environmental impact.

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ChemInform Abstract: A Mild and Efficient Synthesis of 3‐Aminosubstituted Isothiazole S‐Oxides and Their 5‐Sulfanylsubstituted Derivatives.

et al. 2009

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A Mild and Efficient Synthesis of 3-Aminosubstituted Isothiazole S-Oxides and their 5-Sulfanylsubstituted Derivatives

Cited by 5 publications

References 11 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

Fused Isothiazole S‐Oxide Systems from Cycloaddition Reactions of N‐Benzylisothiazol‐3‐amine 1‐Oxide

ChemInform Abstract: A Mild and Efficient Synthesis of 3‐Aminosubstituted Isothiazole S‐Oxides and Their 5‐Sulfanylsubstituted Derivatives.

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