One-pot synthesis of functionalized dihydroindolizinones from pyrrolylpropynoates and diethyl aminomalonate

Mendeleev Communications, Год журнала: 2025, Номер 35(1), С. 99 - 101

Опубликована: Янв. 1, 2025

Язык: Английский

---

Dearomative Ring-Opening of N-Fused Heteroarenes: Access to Tetrasubstituted Alkenes and Ketimines

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 15, 2025

We report a novel and efficient strategy for constructing tetrasubstituted alkenes α-iminonitriles from 3-aminoindolizines 3-aminoimidazo[1,2-a]pyridines. This approach involves dearomative ring-opening of N-fused heteroaromatic amines coupled to DDQ-mediated oxidative process under mild, metal-free conditions. The methodology demonstrates broad substrate scope, excellent functional group tolerance, scalability, offering versatile platform synthesizing complex nitrile-containing frameworks.

Язык: Английский

---

Fast and efficient one-pot ultrasound-mediated synthesis of solid state (full color tunable) fluorescent indolizine derivatives

Dyes and Pigments, Год журнала: 2023, Номер 216, С. 111332 - 111332

Опубликована: Апрель 24, 2023

Язык: Английский

---

Recent advances in the synthesis of N-fused heterocycles from N-aroylmethylpyrrole-2-carboxaldehyde derivatives via annulative functionalization strategies

Tetrahedron, Год журнала: 2023, Номер 151, С. 133787 - 133787

Опубликована: Дек. 19, 2023

Язык: Английский

---

Synthesis and Photochemical Characterization of Indolizine Fluorophores Obtained by a Multicomponent Palladium Iodide−Catalyzed Oxidative Aminocarbonylation Approach

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(12)

Опубликована: Янв. 19, 2024

Abstract A catalytic carbonylative method for the direct, multicomponent synthesis of indolizine fluorophores has been developed. The process is based on PdI 2 /KI‐catalyzed oxidative aminocarbonylation 2‐(pyridin‐2‐yl)pent‐4‐yn‐1‐carbonyl compounds leading to corresponding 2‐ynamide intermediates, followed in situ by 5‐ exo ‐ dig cyclization (by amine‐promoted conjugate addition pyridine ring nitrogen) and aromatization, give finally isolated N , ‐disubstituted 2‐(indolizin‐3‐yl)acetamides. Reactions are carried out under relatively mild conditions (100 °C 20 atm a 4 : 1 mixture CO−air 6–15 h) MeCN as solvent with low catalyst loading (0.33 mol% ), presence 0.5 equiv. KI 3 secondary amine. optical properties representative 2‐(indolizin‐3‐yl)acetamide products have also investigated.

Язык: Английский

---

Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes

Molecules, Год журнала: 2024, Номер 29(9), С. 2061 - 2061

Опубликована: Апрель 29, 2024

Herein, we have developed a new approach for the synthesis of indolizine via Cu-catalyzed reaction pyridine, acetophenone, and nitroolefin under mild conditions in high yields. This involved formation C–N C–C bonds compounds with stereoselectivity excellent functional group tolerance.

Язык: Английский

---

Reactions of Electrophilic Allenoates [and Isocyanates/Isothiocyanates] with a 2-Alkynylpyridine via a Free Carbene Intermediate

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7805 - 7808

Опубликована: Сен. 10, 2024

A pyridine containing a 2-alkynyl substituent armed with carbene reporter group [R

Язык: Английский

---

Visible‐Light‐Induced Insertion of Sulfur Dioxide Mediated by Electron Donor–Acceptor Complex: Synthesis and Photophysical Properties of 3‐Sulfonyl Indolizines

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(22)

Опубликована: Апрель 19, 2023

Abstract This work investigates a light‐driven 3‐component sulfonylation reaction of indolizines without needing any external photocatalyst. The mechanistic investigations support the formation an electron donor–acceptor (EDA) complex in situ. transformation offers mild and sustainable approach with high functional group tolerance for synthesis 3‐sulfonylated indolizines. compound class has valuable photophysical properties represents promising candidates various applications related to fluorescence.

Язык: Английский

---

Unveiling [3 + 2] cycloaddition reactions of pyridinium bis(methoxycarbonyl)methylides and pyridinium dicyanomethylides with cyclooctyne for indolizine synthesis from the molecular electron density theory perspective

Structural Chemistry, Год журнала: 2023, Номер 35(2), С. 455 - 469

Опубликована: Июнь 6, 2023

Язык: Английский

---

Indolizinylalanine Regioisomers: Tryptophan Isosteres with Bathochromic Fluorescence Emission

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(20), С. 14665 - 14672

Опубликована: Сен. 23, 2024

We have developed a high yielding synthesis of indolizine and directly elaborated the molecule into three optically active indolizinylalanine regioisomers. The protocols exploit metal catalyzed coupling indolizinyl-halides with organozinc reagents derived from carbamoylated iodoalanine esters. scalable provide products in form amenable to solid-phase peptide (SPPS). When incorporated peptides, heterocycle is more basic markedly less nucleophilic than tryptophan. Its protonated vinylpyridinium deeply colored solution while neutral highly fluorescent. fluorescence quantum yield exceeds that indole aza-indoles water, suggesting indolizinylalanines could be powerful optical probes protein structure dynamics, functioning as true tryptophan isosteres.

Язык: Английский

---