Selective C–H chalcogenation of thiazoles <i>via</i> thiazol-2-yl-phosphonium salts

Zi, You; Wagner, K.; Schömberg, Fritz; Vilotijević, Ivan

doi:10.1039/d0ob00684j

Cited by 10 publications

(3 citation statements)

References 86 publications

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“…An interesting example of C2-H-functionalization of thiazoles using phosphines was reported recently [108]. The intermediate triflate phosphonium salts (Scheme 49) were treated with thiols, which form the corresponding thiolates by treatment with sodium hydride.…”

Section: Scheme 46mentioning

confidence: 99%

“…The intermediate triflate phosphonium salts (Scheme 49) were treated with thiols, which form the corresponding thiolates by treatment with sodium hydride. The reactions proceed under mild conditions; the starting triphenylphosphine can be recovered, the yield varied from low (21%) to quantitative An interesting example of C2-H-functionalization of thiazoles using phosphines was reported recently [108]. The intermediate triflate phosphonium salts (Scheme 49) were treated with thiols, which form the corresponding thiolates by treatment with sodium hydride.…”

Section: Scheme 46mentioning

confidence: 99%

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Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

2021

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The review is devoted to modern trends in the chemistry of 2-amino and 2-mercapto substituted benzothiazoles covering the literature since 2015. The reviewed heterocycles belong to biologically active and industrially demanded compounds. Newly developed synthesis methods can be divided into conventional multistep processes and one-pot, atom economy procedures, realized using green chemistry principles and simple reagents. The easy functionalization of the 2-NH2 and 2-SH groups and the benzene ring of the benzothiazole moiety allows considering them as highly reactive building blocks for organic and organoelement synthesis, including the synthesis of pharmacologically active heterocycles. The review provides a summary of findings, which may be useful for developing new drugs and materials and new synthetic approaches and patterns of reactivity.

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Section: Scheme 46mentioning

confidence: 99%

Section: Scheme 46mentioning

confidence: 99%

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

2021

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“…[16][17][18] Most of these endeavors however were limited to pyridylphosphonium salts. We wondered whether a thiazolylphosphonium salt, [19] which is a rarely used heterocyclic electrophile, could be a competent coupling partner in these reductive functionalization reactions, as this could establish a general, practical and synthetically useful protocol for the assembly of C2-alkylated benzothiazoles. Manganese is an inexpensive, relatively non-toxic, earth-abundant transition metal that shows promise as a reductant for reductive functionalization between two electrophiles without the aid of other transition-metal catalysts (such as nickel, cobalt) or ligands.…”

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Manganese‐Mediated Reductive Alkylation of Thiazolyl‐Phosphonium Salts

et al. 2023

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Reductive functionalization reactions between two electrophiles is a straightforward protocol to access carbon‐carbon bonds without use of organometallic reagents prepared in advance. Here, we developed a manganese‐mediated reductive alkylation of heterocyclic thiazolyl‐phosphonium salts with benzyl bromides to form C2‐alkylated benzothiazoles. The reaction features a broad substrate scope, high‐functional‐group tolerance, and can be utilized in late‐stage modification of complex natural products and bioactive molecules.

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Accessing 2‐(Chalcogen)benzothiazoles via Electrochemical Intermolecular Cyclization of Isocyanides with Thiols or Diselenides

Zhang,

Mo,

Tang

et al. 2024

Adv Synth Catal

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2‐(chalcogen)benzothiazoles are frequently used as core structures for the development of pharmaceutical agents. A mild strategy for the synthesis of 2‐(chalcogen)benzothiazoles under electrooxidative conditions using isocyanides, thiols or diselenides as substrates was developed. This protocol allows access to structurally diverse 2‐(chalcogen)benzothiazoles in good yields and with good functional group tolerance, which does not require heavy metal catalysts and exogenous oxidants. Furthermore, gram‐scale synthesis was performed to demonstrate the scale‐up applicability of this reaction.

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Selective C–H chalcogenation of thiazoles via thiazol-2-yl-phosphonium salts

Abstract: Medicinally relevant substituted benzothiazoles and thiazoles are prepared under mild conditions by a regioselective C2–H chalcogenation via preparation of the phosphonium salt and the subsequent reaction with S- and Se-centered nucleophiles.

Cited by 10 publications

References 86 publications

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

Manganese‐Mediated Reductive Alkylation of Thiazolyl‐Phosphonium Salts

Accessing 2‐(Chalcogen)benzothiazoles via Electrochemical Intermolecular Cyclization of Isocyanides with Thiols or Diselenides

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