Tribromo Phloroglucinol as a Novel and Highly Efficient Reagent for the Conversion of Benzothioamides to the Corresponding 1,2,4-Thiadiazoles

Zali‐Boeini, Hassan; Mansouri, Seyed Gholamhossein

doi:10.1080/00397911.2015.1040512

Cited by 9 publications

(3 citation statements)

References 15 publications

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“…TCPG shown in Figure 1 is enol-form, while 2,4,6trichlorocyclohexane-1,3,5-trione can be formed through the tautomerization of TCPG. 61,62 We postulate that the tautomerization of TCPG plays an important role in the formation of C 2 O in high conversion. The chloride at the αposition of the carbonyl group formed by the tautomerization is much more reactive than the aryl chloride in TCPG, which facilitates S N Ar reaction (Figure S1, Supporting Information).…”

Section: Characterization Of C 2 Omentioning

confidence: 99%

Covalent-Frameworked 2D Crown Ether with Chemical Multifunctionality

Kim,

Park

et al. 2024

J. Am. Chem. Soc.

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Here, we present the synthesis and characterization of a novel 2D crystalline framework, named C 2 O, which mainly consists of carbon and oxygen in a 2:1 molar ratio and features crown ether holes in its skeletal structure. The covalentframeworked 2D crown ether can be synthesized on a gram-scale and exhibits fine chemical stability in various environments, including acid, base, and different organic solvents. The C 2 O efficiently activates KI through the strong coordination of K + with crown ether holes in a rigid framework, which enhances the nucleophilicity of I − and significantly improves its catalytic activity for CO 2 fixation with epoxides. The presence of C 2 O with KI results in remarkable increases in CO 2 conversion from 5.7% to 99.9% and from 2.9% to 74.2% for epichlorohydrin and allyl glycidyl ether, respectively. Moreover, C 2 O possesses both electrophilic and nucleophilic sites at the edge of its framework, allowing for the customization of physicochemical properties by a diverse range of chemical modifications. Specifically, incorporating allyl glycidyl ether (AGE) as an electrophile or ethoxyethylamine (EEA) as a nucleophile into C 2 O enables the synthesis of C 2 O-AGE or C 2 O-EEA, respectively. These modified frameworks exhibit improved conversions of 97.2% and 99.9% for CO 2 fixation with allyl glycidyl ether, outperforming unmodified C 2 O showing a conversion of 74.2%. This newly developed scalable, durable, and customizable covalent framework holds tremendous potential for the design and preparation of outstanding materials with versatile functionalities, rendering them highly attractive for a wide range of applications.

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Section: Characterization Of C 2 Omentioning

confidence: 99%

Covalent-Frameworked 2D Crown Ether with Chemical Multifunctionality

Kim,

Park

et al. 2024

J. Am. Chem. Soc.

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“…[39] In 2015, Boeini and Mansouri used an unusual reagent -2,4,6-tribromo-1,3,5-trihydroxybenzene (TBTHB, 44) -for the rapid (15-20 min) and extremely efficient conversion (yields up to 98 %) of a series of benzothioamide derivatives 45 into the corresponding 3,5-diaryl-1,2,4-thiadiazoles 46 (Scheme 19). [40] During this synthetic process, hexahydroxybenzene is formed as a relatively valuable by-product. This protocol seems to be one of the simplest and fastest routes for the preparation of 3,5-diaryl-1,2,4-thiadiazoles so far developed.…”

Section: Synthesis Of 124-thiadiazoles By Dimerization Of Thioamidesmentioning

confidence: 99%

Building 1,2,4‐Thiadiazole: Ten Years of Progress

2017

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Thiadiazoles are among the privileged pharmacological building blocks due to their unique chemical properties for diverse biological and clinical applications. 1,2,4‐Thiadiazole derivatives have recently attained a therapeutic and economic importance that they did not possess a few years ago, thus leading to growing interest in this class of heterocycles. Moreover, the importance of such molecules is not restricted to medicinal chemistry; they also perform well as N,S ligands in coordination chemistry or as important intermediates for fine‐chemicals synthesis. In this context, this review systematizes the main advances in the synthesis of 1,2,4‐thiadiazole‐based compounds in the last ten years and discloses some relevant applications of these compounds during that period.

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“…The synthetic utility of alkenes is further augmented by their availability from commercial sources or reliable synthetic operations . A range of thioamides are also commercially available or readily synthesized from their amide counterparts with sulfurating agents . To circumvent the β-aminothiol availability problem in thiazoline synthesis, the development of a general coupling reaction between alkenes and thioamides would provide versatile access to a wide array of thiazoline structures (Scheme c) .…”

mentioning

confidence: 99%

One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides

Alom

2017

Org. Lett.

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A convenient synthesis of a privileged pharmaceutical motif, thiazoline is accomplished. This reaction utilizes simple and readily available alkene and thioamide substrates in an intermolecular fashion via a simple one-pot procedure. A wide range of functional groups is tolerated, and the thiazoline product has been further utilized for the synthesis of the corresponding β-aminothiol and thiazole from routine hydrolysis and oxidation protocols.

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Tribromo Phloroglucinol as a Novel and Highly Efficient Reagent for the Conversion of Benzothioamides to the Corresponding 1,2,4-Thiadiazoles

Cited by 9 publications

References 15 publications

Covalent-Frameworked 2D Crown Ether with Chemical Multifunctionality

Covalent-Frameworked 2D Crown Ether with Chemical Multifunctionality

Building 1,2,4‐Thiadiazole: Ten Years of Progress

One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides

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