Reaction of N, N-dichlorosulfonamides with aryl isothiocyanates

Cherkasov, V. M.; Dashevskaya, T. A.; Baranova, L. I.

doi:10.1007/bf01031791

Cited by 2 publications

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“…Fortunately, with the use of EtOH as a solvent and inclusion of a ligand, the protocol can transform a similar range of sulfamide substrates and allows the efficient cross-coupling of electronically varied (hetero)aryl bromides (Scheme ). Specifically, para- and meta-substituted N- aryl sulfamides 3l and 3m were synthesized with similar or improved yields relative to those reported previously . As anticipated under the developed sulfamide arylation conditions, aryl bromides can react, without engaging either C(sp 2 )–B or C(sp 2 )–Cl bonds, to afford products 3e and 3n with useful synthetic handles for further functionalization.…”

Section: Resultsmentioning

confidence: 99%

“… a General conditions: sulfamide 1 (1.0 equiv), (hetero)aryl bromide (1.5 equiv), [Ir(ppy) 2 (dtbbpy)]PF 6 (1 mol %), NiBr 2 ·glyme (10 mol %), dtbbpy (4 mol %), and DBU (3.0 equiv) in EtOH (0.25 M) with stirring between two 34 W blue Kessil lamps for 24–96 h. b Isolated yield when prepared from N , N -dichlorosulfamide c Isolated yield when prepared from sulfamic acid …”

Section: Resultsmentioning

confidence: 99%

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Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

et al. 2020

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A general method for the N-arylation of sulfamides with aryl bromides is described.The protocol leverages a dual-catalytic system of nickel and a photoexcitable iridium complex and proceeds at room temperature under visible light irradiation. Using these tactics, aryl boronic esters and aryl chlorides can be carried through the reaction untouched. Thereby, this method complements known Buchwald-Hartwig coupling methods for N-arylation of sulfamides.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

et al. 2020

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“…The following compounds were prepared by the literature methods cited: N -benzoylbenzamidine ( 15a ), N -acetylbenzamidine ( 15c ), N -benzoylacetamidine ( 15e ), 1-(ethoxycarbonyl)formamidine hydrobromide, 1,1-bis(ethoxycarbonyl)formamidine hydrochloride, N -thiobenzoylbenzamidine ( 29a ), hydrochloride salt of N -thiobenzoylacetamidine ( 29b ), hydrochloride salt of N , N -dimethylformamidine ( 42 )…”

Section: Methodsmentioning

confidence: 99%

1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹

Guzmán¹,

Romero²,

Talamás³

et al. 1996

J. Org. Chem.

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Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4π + 2π] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on heating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the 1H-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by 1H NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes. These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.

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Reaction of N, N-dichlorosulfonamides with aryl isothiocyanates

Cited by 2 publications

References 1 publication

Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹

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Reaction of N, N-dichlorosulfonamides with aryl isothiocyanates

Cited by 2 publications

References 1 publication

Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines1

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1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹