Electrochemical Decarboxylative Addition of N‐Aryl Glycines to Enaminones: Access to C3‐Aminomethyl Chromones

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(28)

Опубликована: Май 1, 2024

Abstract An electrochemical decarboxylative addition of N ‐substituted glycines to enaminones has been developed and conducted under oxidant‐, catalyst‐, light‐free conditions in acetonitrile at room temperature by using electron as the traceless oxidant, which provided a green approach access C3‐aminomethyl chromones. The resulting products were formed through radical addition/oxidation/cyclization or electrophilic addition/cyclization pathway could act valuable building blocks construct polysubstituted pyrimidine derivatives.

Язык: Английский

---

Eco-Friendly and Efficient Synthesis of 2-Hydroxy-3-Hydrazono-Chromones Through α,β-C(sp2)–H Bond Difunctionalization/Chromone Annulation Reaction of o-Hydroxyaryl Enaminones, Water, and Aryldiazonium Salts

Molecules, Год журнала: 2025, Номер 30(6), С. 1194 - 1194

Опубликована: Март 7, 2025

A novel, eco-friendly, and efficient method for constructing 2,3-disubstituted chromone skeletons from readily available water, o-hydroxyaryl enaminones (o-HPEs), aryldiazonium salts has been developed under mild reaction conditions. This α,β-C(sp2)–H bond difunctionalization/chromone annulation strategy is achieved by building two C(sp3)–O bonds a C(sp2)-N bond, which provides practical pathway the preparation of 2-hydroxy-3-hydrazono-chromones in moderate to excellent yields, enabling broad substrate scope good functional group tolerance, as well gram-scale synthesis. protocol offers valuable tool synthesizing diverse functionalized chromones with potential applications drug discovery industrial

Язык: Английский

---

Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11627 - 11636

Опубликована: Авг. 9, 2023

Syntheses of highly functionalized 4-alkylated 1,4-dihydropyridines (1,4-DHPs) from cyclic ethers and enaminones via iron(II)-mediated oxidative free radical cascade C(sp3)-H bond functionalization/C(sp3)-O cleavage/cyclization reaction have been first developed. This novel synthetic strategy offers an alternative method for the construction 1,4-DHPs by using esters as C4 sources, well expands application in heterocycle synthesis.

Язык: Английский

---

An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110784 - 110784

Опубликована: Дек. 1, 2024

Язык: Английский

---

Gold-Catalyzed Reactions of Enynals with Alkenes for Synthesis Binaphthyl Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6074 - 6084

Опубликована: Апрель 16, 2024

A PPh3Au[B(C6F5)4]-catalyzed reaction of enynals and alkenes for the construction binaphthyl derivatives was described. This transformation achieved through o-Quinodimethane (o-QDM) intermediate's extended conjugated addition process. The has advantages wide substrate scopes, mild conditions, high efficiency, good scalability.

Язык: Английский

---

Domino Approach to Heterocycles-Based Unsymmetrical Triarylmethanes through Heteroannulation of 2-(2-Enynyl)-pyridines with Enaminones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12104 - 12117

Опубликована: Авг. 13, 2024

Herein, we report a copper-catalyzed protocol to access unsymmetrical triarylmethanes containing both indolizine and the chromone scaffolds in same molecule via 5-endo-dig cyclization of 2-(2-enynyl)-pyridines followed by reaction with 2-hydroxyaryl enaminones. A variety enaminones were subjected under optimal conditions, respective obtained good excellent yields.

Язык: Английский

---

TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[ b ][1,8]naphthyridin derivatives via metal free Cascade annulation

Synthetic Communications, Год журнала: 2024, Номер 54(15), С. 1252 - 1262

Опубликована: Июль 22, 2024

Язык: Английский

---

Synthesis of functionalized tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones through base-promoted annulation of quinoline-derived dipolarophiles and cyclic enaminones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(48), С. 9524 - 9529

Опубликована: Янв. 1, 2023

An eco-friendly and metal-free method for the synthesis of tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones was established. Quinoline-derived dipolarophiles cyclic enaminones as starting materials undergo a 1,4-Michael addition/SNAr tandem annulation reaction affording target products. This approach features transition conditions, good functional group tolerance operational simplicity.

Язык: Английский

---

Diastereoselective Three-Component 1,3-Dipolar Cycloaddition to Access Functionalized β-Tetrahydrocarboline- and Tetrahydroisoquinoline-Fused Spirooxindoles

Molecules, Год журнала: 2024, Номер 29(8), С. 1790 - 1790

Опубликована: Апрель 15, 2024

A chemselective catalyst-free three-component 1,3-dipolar cycloaddition has been described. The unique polycyclic THPI and THIQs were creatively employed as dipolarophiles, which led to the formation of functionalized β-tetrahydrocarboline- tetrahydroisoquinoline-fused spirooxindoles in 60–94% yields with excellent diastereoselectivities (10: 1−>99: 1 dr). This reaction not only realizes a concise THPI- or THIQs-based cycloaddition, but also provides practical strategy for construction two distinctive spirooxindole skeletons.

Язык: Английский

---

Iridium-catalyzed reduction of o-hydroxyl phenyl enaminones for the synthesis propiophenones and their application in 3-methyl chromone synthesis

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A method of reducing

Язык: Английский

---