Electrophilic Thiocyanation of Aromatic, Heteroaromatic and Aliphatic Compounds: A Novel Perspective on Recent Advances

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134645 - 134645

Опубликована: Апрель 1, 2025

Язык: Английский

---

Cascade Reaction of Tertiary Enaminones, KSCN, and Anilines: Temperature-Controlled Synthesis of 2-Aminothiazoles and 2-Iminothiazoline

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(14), С. 9171 - 9183

Опубликована: Июль 5, 2022

A one-pot cascade strategy for the synthesis of 2-aminothiazole derivatives by tertiary enaminones, KSCN, and anilines was developed. By changing reaction temperature, three-component could be transformed in different ways to obtain moderate good yields polysubstituted 2-aminothiazoles 2-iminothiazolines. This protocol provides an efficient concise approach accessing with potential bioactivity from readily accessible building blocks reagents.

Язык: Английский

---

An environmentally benign way to synthesize 2-thiocyano-1,3-dicarbonyl compounds with high antifungal activity: a key role of solvent

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(17), С. 3615 - 3622

Опубликована: Янв. 1, 2023

The introduction of thiocyano groups into organic molecules is important for the preparation many active ingredients and synthetic intermediates. A commonly used attractive strategy nucleophilic substitution halogens with SCN anion or oxidative thiocyanation using an excess amount external oxidants. sustainable alternative to stoichiometric reagents electrochemistry based on anodic oxidation other Electrochemical various compounds, carried out in usual non-acidic solvents, well known. Here, we present electrochemical 1,3-dicarbonyl compounds which high efficiency was only achieved AcOH as solvent. Electrolysis proceeds undivided cell under constant current conditions without any additional halogen-containing electrolytes. Ammonium thiocyanate source group electrolyte. begins generation (SCN)2 from anion, followed by addition thiocyanogen double bond enol tautomer finally gives products. variety thiocyanated bearing different functional were obtained 37-82% yields shown exhibit antifungal activity.

Язык: Английский

---

Electrosynthesis of Thiocyanated/Iodinated/Brominated Pyrazol‐5‐amines and Thiocyanated Enamines via C(sp²)−H Functionalization

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1782 - 1787

Опубликована: Май 11, 2023

Abstract An electrochemical method for the C( sp 2 )−H thiocyanation of pyrazol‐5‐amines and enamines were developed in an undivided cell. A variety thiocyanated pyrazol‐5‐amine enamine derivatives accessed 36–91% yields, employing thiocyanate salts as electrolyte thiocyanating reagent. Moreover, this protocol can be extended to synthesis various iodinated brominated 51–95% yields. This does not require a metal or external chemical oxidants tolerates unprotected amino groups.

Язык: Английский

---

Electrochemical oxythiocyanation of ortho-olefinic amides: Access to diverse thiocyanated benzoxazines

Tetrahedron Letters, Год журнала: 2023, Номер 116, С. 154341 - 154341

Опубликована: Янв. 2, 2023

Язык: Английский

---