Facile, efficient and eco-friendly synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles

Kuhn, Bruna L.; Fortes, Margiani P.; Kaufman, Teodoro S.; Silveira, Cláudio C.

doi:10.1016/j.tetlet.2014.01.101

Cited by 23 publications

(4 citation statements)

References 67 publications

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“…2, 134.2, 126.5, 124.1, 119.6, 115.6, 115.4, 112.1, 90. 9, 136.6, 127.8, 122.9, 121.3, 117.9, 111.2, 88.0, 33. 1-Phenyl-3-thiocyanato-1H-indole (2n). 15 The general procedure was followed using 1-phenyl-1H-indole (94.2 mg, 0.488 mmol) as the starting material. Purification by column chromatography yielded 2n (107.3 mg, 88%) as a pale yellow oil.…”

Section: Ms (Esi) M/zmentioning

confidence: 99%

A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles

et al. 2014

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Section: Ms (Esi) M/zmentioning

confidence: 99%

A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles

et al. 2014

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“…The direct trifluoromethylthiolation of thiocyanate derivate 4 was performed in the presence of the Ruppert -Prakash reagent (TMSCF 3 ), affording the 3-[(trifluoromethyl)sulfanyl]-1H-indole (12) in 86 % yield. [57] In another synthetic transformation, derivate 4 has been involved in a [3 + 2]-cycloaddition with sodium azide under zinc bromide promotion [58] allowing the formation of sulfenyl tetrazole 13 in 80 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…In another synthetic transformation, derivate 4 has been involved in a [3+2]‐cycloaddition with sodium azide under zinc bromide promotion [58] allowing the formation of sulfenyl tetrazole 13 in 80 % yield.…”

Section: Resultsmentioning

confidence: 99%

Immobilized Rose Bengal as Photocatalyst for Metal‐Free Thiocyanation of Azaheterocycles under Continuous Flow Conditions

Colombo,

Fiorenza Boselli,

Raimondi

et al. 2023

Helvetica Chimica Acta

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The immobilization of Rose Bengal onto Merrifield resin and its application in the light‐driven metal‐free thiocyanation of azaheterocycles in continuo were investigated. The supported photocatalyst was used in batch reactions under heterogeneous conditions, with different azaheterocycles, and proved to efficiently promote the reaction. The resin‐supported Rose Bengal was then employed under continuous flow conditions, affording thiocyanate functionalized azaheterocycles with higher space‐time‐yields than the in‐batch transformations, and in a shorter reaction time. The easily modification of the SCN groups was also demonstrated by synthetizing trifluoromethyl thioethers and sulfenyl tetrazoles derivates in high yields.

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“…Hence, compounds 3 a, 3 c, 3 e, 3 f and 5 f were taken as models and submitted to a mild thiocyanation reaction with NH 4 SCN and oxone as oxidizing agent (3 equiv. each) in MeOH at room temperature (Table ) …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antifungal Activity of 4‐ and 6‐(1H‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

et al. 2019

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Facile and efficient syntheses of 4‐(1H‐pyrrol‐1‐yl)‐coumarins and 6‐(1H‐pyrrol‐1‐yl)‐coumarins from the corresponding aminocoumarins are reported. The transformations were optimized and their corresponding scope and limitations were assessed. Selected (1H‐pyrrol‐1‐yl)‐coumarins were further subjected to a mild thiocyanation, undergoing selective functionalization on the pyrrole nucleus. A set of 10 differently substituted compounds was submitted to activity testing against various fungal strains. It was found that the introduction of a SCN moiety increased the antifungal activity, turning some compounds into fungicidal agents, to the point that one of the thiocyanato derivatives displayed an antifungal profile comparable to those of fluconazole and nystatin.

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Facile, efficient and eco-friendly synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles

Cited by 23 publications

References 67 publications

A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles

A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles

Immobilized Rose Bengal as Photocatalyst for Metal‐Free Thiocyanation of Azaheterocycles under Continuous Flow Conditions

Synthesis and Antifungal Activity of 4‐ and 6‐(1H‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

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