Synthesis of Naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C–H Functionalization of N-Pyridyl-2-pyridones with Diazonaphthalen-2(1H)-ones

Organic Letters, Год журнала: 2024, Номер 26(4), С. 786 - 791

Опубликована: Янв. 22, 2024

Presented herein is an unprecedented synthesis of naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-catalyzed C6/C5 dual C–H functionalization N-pyridyl-2-pyridones with diazonaphthalen-2(1H)-ones. This protocol forms C–C and C–O bonds in one pot which diazonaphthalen-2(1H)-ones serve as bifunctional reagents, providing both alkyl aryloxy sources. To the best our knowledge, this first example title compounds by using substrates. Notably, method features operational simplicity, good functional group tolerance, high efficiency, atom economy.

Язык: Английский

---

Rh(II)-Catalyzed Synthesis of N-Aryl 2-pyridone Using 2-Oxypyridine and Diazonaphthoquinone Via 1,6-Benzoyl Migratory Rearrangement

Organic Letters, Год журнала: 2023, Номер 25(16), С. 2873 - 2877

Опубликована: Апрель 13, 2023

A Rh(II)-catalyzed simple and efficient synthesis of N-arylated 2-pyridone derivatives is described using 2-oxypyridine diazonaphthoquinone as coupling partners. The reaction proceeds through the insertion nitrogen atom derivative into quinoid carbene subsequent 1,6-benzoyl migratory rearrangement. broadened with sufficient scope has potential to offer axially chiral under suitable asymmetric conditions.

Язык: Английский

---

Ruthenium(II)-Catalyzed Sequential C–H/N–H Alkene Annulation Cascade of Phenanthroimidazoles: Synthesis and Photophysical Studies

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6016 - 6026

Опубликована: Апрель 16, 2024

We report ruthenium(II)-catalyzed sequential C–H/N–H alkenylation cascade of phenanthroimidazole and alkenes to form novel phenanthroimidazoisoindol acrylates via dual C–H activation aza-Michael reaction. The two nitrogen atoms the imidazole ring act as directing groups for regioselective ortho activation. These polycyclic N-heterocycles were evaluated their photophysical properties.

Язык: Английский

---

Pd(II)-Catalyzed Three-Component Synthesis of Furo[2,3-d]pyrimidines from β-Ketodinitriles, Boronic Acids, and Aldehydes

Organic Letters, Год журнала: 2023, Номер 25(50), С. 9070 - 9075

Опубликована: Дек. 13, 2023

A Pd(II)-catalyzed three-component synthesis of 2,4,6-triarylfuro[2,3-d]pyrimidines from β-ketodinitriles, boronic acids, and aldehydes has been developed. The participation both nitrile (-CN) groups led to the concurrent construction furo-pyrimidine via formation C-C, C═C, C-O, C-N, C═N bonds. compounds show excellent photoluminescence properties with absorption maxima ranging 348 387 nm emission 468 533 nm. synthetic utility protocol was further demonstrated through a few postsynthetic manipulations.

Язык: Английский

---

Design of 2‐Pyridone Fluorophores for Brighter Emissions at Longer Wavelengths

Chemistry - A European Journal, Год журнала: 2024, Номер 30(15)

Опубликована: Янв. 15, 2024

Abstract The recent discovery of blue fluorophores with high quantum yields based on pyridone structures inspired the development new low‐molecular‐weight bright emissions at tunable wavelengths, which are highly attractive for various applications. In this study, we propose a rational design strategy 2‐pyridone‐based long wavelengths. With detailed understanding positional substitution effects each carbon atom 2‐pyridone core, developed fluorophore (λ abs =377 nm; λ em =433 ϵ=13,200 M −1 cm ; ϕ F =88 %) through C 3 ‐aryl and 4 ‐ester substitutions followed by cyclization. Furthermore, applying intramolecular charge transfer (ICT) principle, invented green ‐ ‐diester 6 substitutions. ICT structure shows large molar absorptivity (ϵ=20,100 ), longer emission wavelength =539 nm), yield (ϕ =74 %), Stokes shift (Δv=5720 comparable to those practical fluorescent probes.

Язык: Английский

---

2‐Hydroxypyridines as N‐ and O‐Nucleophiles in Organic Synthesis

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(2)

Опубликована: Ноя. 6, 2023

Abstract 2‐Hydroxypyridines have emerged as versatile nucleophiles in organic synthesis. The N ‐ and O ‐functionalization of 2‐hydroxypyridines affords straightforward practical methods for the construction ‐substituted 2‐pyridones 2‐hydroxypyridines, which are important structural motifs numerous natural products, pharmaceuticals biologically active compounds. Nonetheless, competition between presents an inevitable formidable challenge. In past few decades, chemoselective and/or has received extensive attention from synthetic community, resulting development elegant effective strategies to address this chemoselectivity. This review provides a summary recent advancements realm transition‐metal organo‐catalyzed, well visible‐light promoted functionalization including ‐alkylation, ‐allylation, ‐arylation, ‐alkenylation, ‐alkenylation.

Язык: Английский

---

Ru(II)-Catalyzed Skeletal Editing of Oxindole with Internal Alkyne To Synthesize C7-Alkylated Indole Derivatives

Organic Letters, Год журнала: 2024, Номер 26(38), С. 8051 - 8056

Опубликована: Сен. 16, 2024

A Ru(II)-catalyzed skeletal editing of oxindole scaffolds was established to afford C7-alkyl acetate indole derivatives using internal alkyne and alkyl alcohol. The developed method is simple, efficient, straightforward. reaction extended substrates having wide chemoselective profiles. When unsymmetrical alkynes were used, promising regioselectivity realized. preliminary mechanistic study revealed that the pathway proceeded by Ru(II)/Ag(I)-catalyzed amide cleavage subsequent oxidative annulation.

Язык: Английский

---

Heterogeneous visible-light photoredox catalysis with NiCl2@g-C3N4 for induced C(sp2)-H/N H cross-dehydrogenative coupling

Molecular Catalysis, Год журнала: 2024, Номер 569, С. 114633 - 114633

Опубликована: Окт. 25, 2024

Язык: Английский

---

Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

ChemistrySelect, Год журнала: 2024, Номер 9(45)

Опубликована: Ноя. 30, 2024

Abstract A concise and practicable route to the synthesis of multisubstituted 2‐pyridones via a four‐component one‐pot stepwise cyclization catalyzed by Cs 2 CO 3 has been developed. During this transformation, two new C‐C bonds C‐N were generated through an intermolecular condensation/aza‐Michael reaction/intermolecular Michael addition/intramolecular sequence. The alternative protocol offers complementary provide series structurally diverse polysubstituted (21 examples) in good excellent yields (52–81%) from easily available raw materials arylamines, dialkyl acetylenedicarboxylate, 1,3‐dicarbonyl compounds, trialkyl orthoformate under mild conditions. It might opportunities for discovery 2‐pyridones‐containing drugs.

Язык: Английский

---