Mechanosynthesis of Pyrrole-2-carboxylic Acids via Copper-Catalyzed Spiroannulation/Ring-Opening Aromatization of 4-Arylidene Isoxazol-5-ones with Enamino Esters

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4189 - 4193

Опубликована: Май 14, 2024

An efficient and practical tandem reaction of 4-arylidene isoxazol-5-ones with enamino esters catalyzed by an inexpensive copper salt has been established in a ball mill. This innovative approach yields diverse array structurally novel pyrrole-2-carboxylic acids, showing excellent tolerance toward different functional groups. By integrating spiroannulation ring-opening aromatization processes, this protocol introduces facile cost-effective strategy for synthesizing highly functionalized pyrrole derivatives.

Язык: Английский

---

Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4229 - 4234

Опубликована: Май 13, 2024

A copper-catalyzed [3 + 2] annulation of

Язык: Английский

---

Synthesis of spiroisoxazoline oxindoles by base-promoted annulation of oxime esters and isatins

Tetrahedron Letters, Год журнала: 2025, Номер 159, С. 155506 - 155506

Опубликована: Март 6, 2025

Язык: Английский

---

Iron-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 2-Hydroxy-1-Naphthoates for the Synthesis of Benzo[g]indoles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

An iron-catalyzed [3 + 2] annulation of O-acyl oximes with 2-hydroxy-1-naphthoates has been developed. This strategy features the simultaneous activation both substrates to form two radical intermediates. Subsequent selective C-N coupling followed by sequential condensation and 1,3-ester migration affords 1H- or 3H-benzo[g]indoles. In terms derived from 4-oxocyclohexanone 4-azacyclohexanone, further ring-opening furnishes 2-(2-hydroxyethyl)- 2-(2-aminoethyl)-1H-benzo[g]indoles.

Язык: Английский

---

Iron-Catalyzed Double Annulation of O-Acyl Oximes with Fumaronitrile for the Synthesis of 4-Cyano-7-azaindoles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Июнь 2, 2025

An iron-catalyzed double annulation of O-acyl oximes with fumaronitrile has been developed for the concise synthesis polysubstituted 4-cyano-7-azaindoles. This method enables construction two fused heterocycles in a one-step reaction using readily available starting materials under redox-neutral conditions.

Язык: Английский

---

Copper-catalyzed [3+2] annulation of O-acyl ketoximes with 2-aryl malonates for the synthesis of 3-aryl-4-pyrrolin-2-ones

Chemical Communications, Год журнала: 2023, Номер 59(35), С. 5225 - 5228

Опубликована: Янв. 1, 2023

A copper-catalyzed [3+2] annulation of O -acyl ketoximes with 2-aryl malonates for the concise synthesis 3-aryl-4-pyrrolin-2-ones has been developed.

Язык: Английский

---

Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13076 - 13088

Опубликована: Авг. 31, 2023

An unexpected copper-mediated radical-induced ring-opening relay cascade carboannulation reaction of [60]fullerene with cyclobutanone oxime esters is presented for the preparation various Cl-/Br-incorporated [60]fullerene-fused cyclopentanes. The unique transformation uses inexpensive copper salts as promoters and halogen sources features simple redox-neutral conditions a broad substrate scope, providing practical access to class novel five-membered carbocycle-fused fullerenes.

Язык: Английский

---

Generation and Radical–Radical Cross-Coupling of Alkenyloxy Radical

Organic Letters, Год журнала: 2024, Номер 26(12), С. 2456 - 2461

Опубликована: Март 19, 2024

Alkene-attached oxygen radicals are rarely used, as highly reactive incompatible with the alkene moiety. The direct radical–radical cross-coupling of O is also challenging (limited to N–O bond formation) because lack suitable persistent radical species. This study demonstrated feasibility using Breslow intermediate (BIR) a capture unstable π-conjugated and allow C–O cross-coupling.

Язык: Английский

---

Copper Catalyzed Heteroannelation Reaction between 4‐Thiazolidinones and O‐Acetyl Oximes to Synthesize 2,5‐Diphenyl‐3‐(Pyrimidin‐2‐yl)‐3,4‐Dihydro‐2H‐Pyrrolo‐[2,3‐d]‐Thiazole

ChemistrySelect, Год журнала: 2024, Номер 9(23)

Опубликована: Июнь 18, 2024

Abstract An intermolecular copper catalyzed heteroannelation reaction using Csp 3 ‐Csp radical coupling approach has been accomplished to synthesize 2,5‐diphenyl‐3‐(pyrimidin‐2‐yl)‐3,4‐dihydro‐2 H ‐pyrrolo[2,3‐ d ]thiazole. C−C between 4‐thiazolidinones and O‐acetyl oximes under Cu catalyst further cyclizes get the target molecule thiazolidine‐fused nucleus. This unified method offers access novel fused heterocycles with pyrimidines bearing 4‐thiazolidinone in moderate higher yields. The optimization study includes various catalysts, oxidants, bases solvents at different temperatures.

Язык: Английский

---

Copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of oximes with α-amino ketones: entry to 3-aminopyrroles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5806 - 5812

Опубликована: Янв. 1, 2024

An unprecedented copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of oximes with α-amino ketones involving dehydroxylation toward 3-aminopyrroles is disclosed.

Язык: Английский

---