Arylsulfonylimine: Darstellung, Eigenschaften und Reaktivität

Albrecht, R.; Kresze, G.; Mlakar, Bogdan

doi:10.1002/cber.19640970224

Cited by 138 publications

(32 citation statements)

References 3 publications

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“…(ii) The preparation of N-(m-nitrophenylglyoxa1)-ptoluenesulfonamide is typical of the preparation of other aroyl N-sulfonylimines and the procedure is due t o Kresze and co-workers (12).…”

Section: Methodsmentioning

confidence: 99%

Reactions of Functionalized 1,3-Dipoles

Lown¹,

Landberg²

1974

Can. J. Chem.

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A new synthetic approach to the formation of 5-5,5-6,s-5-5, and 6-5-6 fused heterocycles employing cycloadditions with functionalized dipoles is described and its scope and utility explored through representative examples. The regiochemistry and stereochen~istry of the additions is established by specific deuterium labelling, n.m.r. spectroscopy, and by chemical means.On dCcrit une nouvelle approche synthetique a la formation des hetCrocycles condenses 5-5, 5-6, 5-5-5 et 6-5-6; la generalit6 et I'utilite de cette methode impliquant des cycloadditions de dipoles fonctionnalises est examine par l'intermidiaire d'exemples reprisentatifs. L a regiosClectivitC et la stereochimie des additions est Btablie i I'aide de marquage par le deuterium de faqon specifique, par r.m.n. et par des moyens chimiques.[ basic reaction to a scheme for the preparation of thermal decomposition of 3-aroylaziridines in linked heterocycles (2) as illustrated in eq. 2 via acetonitrile (3, 4) and in their reaction with consecutive condensation and 1,3-dipolar addi-p-nitrosophenols (4) when 3,5-dihydro-2H-pyrtion. A similar general synthetic scheme for the rolo[3,4-d]oxazoles were obtained in good yield.preparation of fused ring heterocycles would be a valuable extension of the general cycloaddition principle. One approach we wish to explore in this paper is the scope of the reactions of 1,3-dipoles bearing additional functionality (i.e. besides their basic 4n electron reactive system) to form bicyclic heterocycles, as shown in eq. 3. The additional functionalities f and g on the 1,3-dipole and dipolarophile, respectively, should give the potential second fused five-or sixmembered ring provided the reaction has the desired regiochemistry and stereochemistry. Indications of the usefulness of this approach had been obtained during an examination of the O = C H --COArOur initial approach to systematize these findings has been to examine the reaction of aroylazomethine ylides (generated by the thermal electrocyclic cleavage of aziridines) with a range of suitably functionalized dipolarophiles). Exploratory reactions of azomethine oxides (nitrones) are also discussed in this context. For personal use only.

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“…(ii) The preparation of N-(m-nitrophenylglyoxa1)-ptoluenesulfonamide is typical of the preparation of other aroyl N-sulfonylimines and the procedure is due t o Kresze and co-workers (12).…”

Section: Methodsmentioning

confidence: 99%

Reactions of Functionalized 1,3-Dipoles

Lown¹,

Landberg²

1974

Can. J. Chem.

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“…1.2.3.1. D a r s t e l l u n g v o n S u l f o n y l i m i n e n , T e t r a h y d r o p y r i d i n e n , P y r i d i n e n u n d A z e t i d i n e n Beim Erhitzen von N-Sulfinylsulfonamiden (2) rnit Aldehyden ohne or-standige H-Atome werden in guter Ausbeute unter SO2-Abspaltung N-Sulfonylimine (27) erhalten [44,48].…”

Section: Carbodiiinide [37b]unclassified

“…formamidin [48] 2,O g N-Sulfinyl-p-toluolsulfonamid (2.) und 1,5 g Dimethylformamid werden 8 min kraftig erhitzt.…”

Section: N1 N1 -Dimethyl-n2-(p-toluolsulfonyl) -unclassified

Neuere Methoden der präparativen organischen Chemie V. Organische Synthesen mit Imiden des Schwefeldioxids

1967

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“…Furthermore, they are excellent substrates in nucleophilic additions [6], reductions [7], aza Diels-Alder reactions [8], aziridine [9] and oxaziridine synthesis [10], as well as ene reactions [11]. Several routes toward the synthesis of N-sulfonyl imines have been developed via Lewis and Brønsted acid catalyzed reactions of sulfonamides with aldehyde precursors [12], rearrangement of oxime o-sulfinates [13], tellurium mediated reaction of aldehydes with chloramines T by utilization of the in situ generated N,N'-ditosyltellurodiimide [14], application of Nsulfinyl sulfonamides instead of sulfonamides to generate sulfonyl imine in situ via a [2+2] cycloaddition and extrusion of sulfur dioxide [15], generation of sulfonamidosulfones and basic elimination [16], and catalyzed isomerization or rearrangement of N-sulfonyl aziridines [17]. However, most of the reported methods suffer from drawbacks like long reaction times, unsatisfactory yields, harsh conditions, the use of expensive reagents, the use of multi-steps and cumbersome procedures, and no agreement with the green chemistry protocols.…”

Section: Introductionmentioning

confidence: 99%

3-Methyl-1-Sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature

Zolfigol

Khazaei

Moosavi‐Zare

et al. 2010

JICS

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New Brønsted acidic ionic liquid, 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} was used as an efficient, green and reusable catalyst and solvent for the synthesis of N-sulfonyl imines via the condensation of sulfonamides with aldehydes as well as isatin. The reactions proceeded at room temperature and the title compounds were obtained in high to excellent yields and in relatively short reaction times.

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Arylsulfonylimine: Darstellung, Eigenschaften und Reaktivität

Cited by 138 publications

References 3 publications

Reactions of Functionalized 1,3-Dipoles

Reactions of Functionalized 1,3-Dipoles

Neuere Methoden der präparativen organischen Chemie V. Organische Synthesen mit Imiden des Schwefeldioxids

3-Methyl-1-Sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature

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