Sulfidation of Alicyclic and Heterocyclic 1,3-Dicarbonyl Systems

Kappe, Thomas; Schnell, Barbara; Georgieva, Krassimira; Jocham, Brigitte; Mayrhofer, Anna; Nikam, B. P.; Issac, Yvette A.; Langhans, K. P.

doi:10.1080/10426509408034233

Cited by 6 publications

(1 citation statement)

References 4 publications

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“…Both species react with sodium dialkylaminodithiocarbamates to compounds 5. The thioethers 3 can be obtained in a similar fashion by using thiophenolate anions [11,12]. However, these methods cannot compete with the simplicity of the preparations presented here.…”

Section: Introductionmentioning

confidence: 99%

Sulfenylation of Heterocyclic 1,3-Dicarbonyl Compounds

Schnell

Kappe

1999

Monatshefte fuer Chemie

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Anions of heteroaromatic 1,3-dicarbonyl compounds, such as 4-hydoxy-2-quinolones and 4-hydroxy-coumarins, react in DMF in the presence of potassium carbonate with diaryl disul®des to yield 3-arylsulfenyl derivatives. The arylthiolate anions formed in this reaction can be oxidized by air to yield the starting diaryl disul®des again. Tetraalkylthiuram disul®des react in the same manner to yield 3-dialkylaminothiocarbonylthio derivatives of the title compounds. Oxidation of the arylthioderivatives with hydrogen peroxide in sodium hydroxide solution usually leads to sulfoxides, whereas oxidation with peracetic acid affords sulfones.

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Section: Introductionmentioning

confidence: 99%

Sulfenylation of Heterocyclic 1,3-Dicarbonyl Compounds

Schnell

Kappe

1999

Monatshefte fuer Chemie

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A Simple, Convenient One‐Pot Synthesis of Dithio‐Carbamide Derivatives of Heterocyclic 1,3‐Dicarbonyl Systems

Nikam¹,

Kappe

2016

Journal of Heterocyclic Chem

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A various new dithi‐ocarbamides were synthesized from heterocyclic six‐membered 1,3‐dicarbonyl systems, such as 4‐hydroxy‐2,5‐pyranopyridines, 4‐hydroxy‐2‐pyridones, 4‐Hydroxy‐2‐quinolones, 4‐hydroxy‐coumarins, and 4‐hydroxy‐1‐methyl‐2‐quinolones. The dicarbonyl compounds in the presence of anhydrous potassium carbonate in dimethyformamide react with tetraalkylthiuram disulfides to yield 3‐dialkylaminothiocarbonylthio derivatives through a simple, convenient one‐pot reaction. The structures were confirmed by using IR, NMR, and elemental analysis.

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Synthesis of 5‐dialkylaminothiocarbonylthiobarbituric acids and 5‐diethyiaminothiocarbonylthio‐6‐aminouracil

Neilands

Sudmale

Schnell

et al. 1998

Journal of Heterocyclic Chem

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The title compounds are obtained by three different methods. The aminothiocarbonylthiolation of barbituric acids 1 and aminouracil (5) can be accomplished in one step by reaction with thiuram disulfides in the presence of potassium carbonate. On the other hand, compounds 4 can be obtained via the salt of chloro derivative 2 or the corresponding iodonium ylides 3. The aminouracil derivative 7 was obtained in a similar fashion from 5 directly or via iodonium betaine 6.

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Sulfidation of Alicyclic and Heterocyclic 1,3-Dicarbonyl Systems

Cited by 6 publications

References 4 publications

Sulfenylation of Heterocyclic 1,3-Dicarbonyl Compounds

Sulfenylation of Heterocyclic 1,3-Dicarbonyl Compounds

A Simple, Convenient One‐Pot Synthesis of Dithio‐Carbamide Derivatives of Heterocyclic 1,3‐Dicarbonyl Systems

Synthesis of 5‐dialkylaminothiocarbonylthiobarbituric acids and 5‐diethyiaminothiocarbonylthio‐6‐aminouracil

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