✦ LIBER ✦

Sulfenylation of heterocyclic 1,3-dicarbonyl systems: 4-Hydroxy-2-pyrones, 6-hydroxy-4-pyrimidones, 4-hydroxy-2-pyridones, 4-hydroxy-6-pyridazinones, and 5-hydroxy-3-pyrazolones

✍ Scribed by Barbara Schnell; Thomas Kappe

Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 568 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370439

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Anions of enolized heteroaromatic 1,3‐dicarbonyl systems, such as the title compounds 1, 9,14, and 19, react in dimethylformamide in the presence of potassium carbonate with diaryl disulfides 2 to yield arylsulfenyl derivatives (3, 10, 15, 20). The arylthiolate anions 4 formed in this reaction can be oxidized by air to yield the starting disulfides 2 again. Tetraalkylthiuram disulfides 7 react in the same manner to yield dialkylaminothiocarbonylthio derivatives (8, 13, 18) of the title compounds. Oxidation of the arylsulfenyl derivatives with hydrogen peroxide in sodium hydroxide solution usually leads to sulfoxides (5, 11, 16), whereas oxidation with peracetic acid affords sulfones (6, 12, 17).

📜 SIMILAR VOLUMES

ChemInform Abstract: Sulfenylation of He

ChemInform Abstract: Sulfenylation of Heterocyclic 1,3-Dicarbonyl Systems: 4-Hydroxy-2-pyrones, 6-Hydroxy-4-pyrimidones, 4-Hydroxy-2-pyridones, 4-Hydroxy-6-pyridazinones, and 5-Hydroxy-3-pyrazolones.

✍ Barbara Schnell; Thomas Kappe 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

Methyl 5-hydroxy-2-(2-hydroxy-6-methoxy-

Methyl 5-hydroxy-2-(2-hydroxy-6-methoxy-4-methylbenzoyl)-3-methoxybenzoate

✍ Shu, Ren-Geng ;Zhu, Hai-Liang ;Tan, Ren-Xiang 📂 Article 📅 2004 🏛 International Union of Crystallography 🌐 English ⚖ 199 KB

4-hydroxy-2′,4′,6′-trichlorobiphenyl and

4-hydroxy-2′,4′,6′-trichlorobiphenyl and 4-hydroxy-2′,3′,4′,5′-tetrachlorobiphenyl are estrogenic in rainbow trout

✍ David B. Carlson; David E. Williams 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 93 KB

ChemInform Abstract: Synthesis of 2-Aryl

ChemInform Abstract: Synthesis of 2-Aryl-4-hydroxy-5-thio Substituted 1,3-Thiazin-6-ones via Sulfenylation of 2-Aryl-4-hydroxy-(1,3)thiazin-6-ones with Sulfenyl Chlorides.

✍ J. V. N. V. PRASAD 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 2 views

Welkstoffe und Antibiotika. 41. Mitteilu

Welkstoffe und Antibiotika. 41. Mitteilung [1]. 2,4-Dimethoxy-8-hydroxy-, 2,4-dimethoxy-7-hydroxy- und 1,3,4-Trimethoxy-6-hydroxy-9-methyl-phenanthren

✍ Christian Egli; Josef Seres; Kurt Steiner; Salah E. Helali; Emil Hardegger 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 492 KB 👁 1 views

## Abstract Aus den Tetralonen I und XIII wurden auf zwei verschiedenen Wegen die Phenanthrene VIII bzw. VIIIb und XVI hergestellt. Versuche zur Synthese von Orchinol (2,4‐Dimethoxy‐7‐hydroxy‐9,10‐dihydrophenanthren) scheiterten in der partiellen Dehydrierung der tricyclischen Ketone X und XI und f

Ring-transformation reactions of 5-hydro

Ring-transformation reactions of 5-hydroxy-2-oxabicyclo[3.2.0]-heptan-4-ones and 5-hydroxy-2-oxabicyclo[3.2.0]hept-6-en-4-ones

✍ Tetsuro Shimo; Hidemi Minamishin; Kenichi Somekawa 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 196 KB

## Abstract Dehydrochlorination of chlorinated 5‐hydroxy‐2‐oxabicyclo[3.2.0]heptan‐4‐ones, 3a‐c, which were obtained from the photo[2+2]cycloadditions between 4‐hydroxy‐3(2__H__)‐furanone 1 and chloroethylenes, with triethylamine gave 2‐ethenyl‐3(2__H__)‐furanones 4a,b or 2‐(2‐cyanoethyl)‐3(2__H__)