Comparison of conventional and microwave-assisted synthesis of some new sulfenamides under free catalyst and ligand

Yakan, Hasan; Kütük, Halil

doi:10.1007/s00706-018-2261-4

Cited by 8 publications

(4 citation statements)

References 38 publications

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“…13 4-(Phenylthio)morpholine (6a). 29 According to TP2, the target product 6a (69 mg, 71%) was synthesized as a colorless oil and purified by column chromatography (ethyl acetate/petroleum ether = 1:5…”

Section: -Methyl-n-(pyridin-2-yl)benzenesulfonamide (3za)mentioning

confidence: 99%

“…13 4-((4-Chlorophenyl)thio)morpholine (6c). 29 According to TP2, the target product 6c (88 mg, 77%) was synthesized as a colorless oil and purified by column chromatography (ethyl acetate/petroleum ether = 1:5). 1 H NMR (400 MHz, CDCl 3 ): δ (ppm): 7.33−7.30 (m, 2H), 7.27−7.23 (m, 2H), 3.64 (t, J = 8.0 Hz, 4H), 2.87 (t, J = 8.0 Hz, 4H).…”

Section: -(P-tolylthio)morpholine (6b)mentioning

confidence: 99%

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Selective Synthesis of Sulfonamides and Sulfenamides from Sodium Sulfinates and Amines

Feng,

Li,

Liu

et al. 2024

J. Org. Chem.

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An effective method was explored for the selective synthesis of sulfonamides and sulfenamides using sodium sulfinates and amines as starting materials. This method offers mild reaction conditions, a broad substrate scope, high efficiency, and readily accessible materials, making it suitable and an alternative strategy for the preparation of a variety of biologically or pharmaceutically active compounds.

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Section: -Methyl-n-(pyridin-2-yl)benzenesulfonamide (3za)mentioning

confidence: 99%

Section: -(P-tolylthio)morpholine (6b)mentioning

confidence: 99%

Selective Synthesis of Sulfonamides and Sulfenamides from Sodium Sulfinates and Amines

Feng,

Li,

Liu

et al. 2024

J. Org. Chem.

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“…The coupling reaction was influenced by nucleophilic properties and the steric effect of the nucleophile reagents. In the same year, the treatment of amines with N -thiophthalimides led to sulfenamides promoted by 2-ethoxyethanol under microwave irradiation [ 100 ]. Alkylamines, such as morpholine, cyclohexylamine, pyrrolidine, and tert -butylamine were participated in this coupling process.…”

Section: Reviewmentioning

confidence: 99%

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

Doraghi,

Aledavoud,

Ghanbarlou

et al. 2023

Beilstein J. Org. Chem.

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In the field of organosulfur chemistry, sulfenylating agents are an important key in C–S bond formation strategies. Among various organosulfur precursors, N-sulfenylsuccinimide/phthalimide derivatives have shown highly electrophilic reactivity for the asymmetric synthesis of many organic compounds. Hence, in this review article, we focus on the application of these alternative sulfenylating reagents in organic transformations.

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“…Although both sulphur and nitrogen have lone pairs of electrons, the electronegativity of the two atoms differs, leading to bond polarisation and the formation of the reactive S-N bond, which may be broken down into electrophiles and nucleophiles. Some sulfenimides have a role as sulfenyl-transfer reagents and may be used to obtain sulfonamides 13 . N -Alkylthio- and N -arylthioimides are used as sulphur-transfer reagents.…”

Section: Introductionmentioning

confidence: 99%

Inhibitory effects of sulfenimides on human and bovine carbonic anhydrase enzymes

Yakan

Bilir

Çakmak

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of sulfenimide derivatives (1a-i) were investigated as inhibitors of human (hCA-I, hCA-II) and bovine (bCA) carbonic anhydrase enzymes. The compounds were synthesised by the reaction of substituted thiophenols with phthalimide by means of an effective, simple and eco-friendly method and the structures were confirmed by IR, 1 H NMR, 13 C NMR, MS and elemental analysis. All derivatives except for the methyl derivative ( 1b ) exhibited effective inhibitory action at low micromolar concentrations on human isoforms, but only four derivatives ( 1e , 1f , 1h , 1i ) inhibited the bovine enzyme. The bromo derivative ( 1f) was found to be strongest inhibitor of all three enzymes with KI values of 0.023, 0.044 and 20.57 µM for hCA-I, hCA-II and bCA, respectively. Results of our study will make valuable contributions to carbonic anhydrase inhibition studies for further investigations since inhibitors of this enzyme are important molecules for medicinal chemistry.

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Comparison of conventional and microwave-assisted synthesis of some new sulfenamides under free catalyst and ligand

Cited by 8 publications

References 38 publications

Selective Synthesis of Sulfonamides and Sulfenamides from Sodium Sulfinates and Amines

Selective Synthesis of Sulfonamides and Sulfenamides from Sodium Sulfinates and Amines

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

Inhibitory effects of sulfenimides on human and bovine carbonic anhydrase enzymes

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