Arylation of Click Triazoles with Diaryliodonium Salts

Mesoionic carbenes (MICs) of the 1,2,3-triazolylidene type have established themselves as a popular class of compounds over the past decade. Primary reasons for this popularity are their modular synthesis and their strong donor properties. While such MICs have mostly been used in combination with transition metals, the past few years have also seen their utility together with main group elements. In this paper, we present an overview of the recent developments on this class of compounds that include, among others, (i) cationic and anionic MIC ligands, (ii) the donor/acceptor properties of these ligands with a focus on the several methods that are known for estimating such donor/acceptor properties, (iii) a detailed overview of 3d metal complexes and main group compounds with these MIC ligands, (iv) results on the redox and photophysical properties of compounds based on MIC ligands, and (v) an overview on electrocatalysis, redox-switchable catalysis, and small-molecule activation to highlight the applications of compounds based on MIC ligands in contemporary chemistry. By discussing several aspects from the synthetic, spectroscopic, and application point of view of these classes of compounds, we highlight the state of the art of compounds containing MICs and present a perspective for future research in this field.

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“…The N3-aryl substitution is facilitated via copper-catalyzed reaction with an aryl iodonium salt. 24 , 25 …”

Section: Synthesis Of Mics Stability Of Free Mics and General Synthesis Of Mic-containing Compoundsmentioning

confidence: 99%

Chemistry of Compounds Based on 1,2,3-Triazolylidene-Type Mesoionic Carbenes

Maity

Sarkar

2021

JACS Au

106

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“…In 2019, Miha Virant et al described an effective synthesis of 1,3,4-trisubstituted-1,2,3-triazole involving alkyne, azide, and aryl iodonium salt with the yield of 83% ( Virant and Kosmrlj, 2019 ). The reaction had the advantages of simple operation and broad scope of substrates, which supplied a robust, selective, and effective method for the synthesis of various bioactive 1,3,4-triaryl-1,2,3-triazolium salts ( Scheme 5D ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis methods of 1,2,3-/1,2,4-triazoles: A review

et al. 2022

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Triazole, comprising three nitrogen atoms and two carbon atoms, is divided into two isomers 1,2,3-triazole and 1,2,4-triazole. Compounds containing a triazole are one of the significant heterocycles that exhibit broad biological activities, such as antimicrobial, analgesic, anti-inflammatory, anticonvulsant, antineoplastic, antimalarial, antiviral, antiproliferative, and anticancer activities. A great quantity of drugs with a triazole structure has been developed and proved, for example, ketoconazole and fluconazole. Given the importance of the triazole scaffold, its synthesis has attracted much attention. This review summarizes the synthetic methods of triazole compounds from various nitrogen sources in the past 20 years.

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“…Triazole is an organic compound containing in their structure a five-membered diunsaturated ring consisting of three nitrogen atoms and two carbon atoms at not contiguous positions. It has pair of isomeric are: 1,2,4-Triazole and1,2,3-Triazole with molecular formulaC2H3N3 [10].…”

Section: Introductionmentioning

confidence: 99%

Untitled

2022

J. Med. Chem. Sci.

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In this research study, new heterocyclic derivatives have been prepared. The most available (Levofloxacin) reacted with thionyl chloride to get acetyl chloride (S1 compound). All the synthesized compounds have been identified using FT-IR and 1 H-NMR spectrum. (Scheme 1) shows that, (S1) compound in the first line treated with thiosemecarbazide to get (S2) hydrazine carbo thio amide derivative then a ring closer reaction has been made to compound (S2) by NaOH solution to get the triazole-3-thiol ring compound (S3). Second-line compound S1 treated with amino acid (glycine) to get (S4) compound. (S5) the compound has been synthesized by reacting (S4) compound with an aromatic aldehyde in the presence of acetic anhydride to get Oxazole ring (S5 compound). Second-line compound (S) treated with hydrazine hydrate to give (S6) compound then a ring closer reaction have been made using carbon disulfide and hydrazine hydrate in basic media to get (S7). Also, (S7) compound reacted with malic anhydride to prepare triazolidine di acetic acid derivative S8 compound. Also, (S) compound treated with semecarbazide and thiosemecabazide in the presence of phosphoryl chloride (POCl3) to get oxadiazole and thiadiazol containing compound respectively (S9, S10). The synthesized compounds antibacterial activity and antioxidant activity (S1-S10) were examined using the (DPPH) technique. The compounds show substantial antioxidant activity equivalent to the well-known (ascorbic acid) (IC50=31.95 g/mL) employed.

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Arylation of Click Triazoles with Diaryliodonium Salts

Cited by 17 publications

References 65 publications

Chemistry of Compounds Based on 1,2,3-Triazolylidene-Type Mesoionic Carbenes

Chemistry of Compounds Based on 1,2,3-Triazolylidene-Type Mesoionic Carbenes

Synthesis methods of 1,2,3-/1,2,4-triazoles: A review

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