Palladium-Catalyzed Aminocyclization–Coupling Cascades: Preparation of Dehydrotryptophan Derivatives and Computational Study DOI Creative Commons
Belén Vaz, Claudio Martínez, Francisco Cruz

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(13), P. 8766 - 8785

Published: June 14, 2021

Dehydrotryptophan derivatives have been prepared by palladium-catalyzed aminocyclization-Heck-type coupling cascades starting from

Language: Английский

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms DOI
Lvyin Zheng,

Kailiang Tao,

Wei Guo

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 363(1), P. 62 - 119

Published: Oct. 31, 2020

Abstract The use of clean and renewable light sources is increasingly common in organic synthesis due to its safety, practicality economy. Recently, photoredox catalysis has shown great application values transformations because advantages environmentally friendly abundant resources. Indoles their derivatives (indolines, oxindoles isatins) are the core skeletons some important compounds widely‐present various natural products pharmaceuticals with different biological activities. Therefore, research on modification indoles particularly for chemists pharmacologists. This review summarizes effects photocatalysis indole recent decades. These accomplished by using metal photocatalysts ( i. e ., Ir, Ru, Ni, Cu, Fe, Au, Rh, TiO 2 , etc.) or non‐metallic Rose Bengal, Eosin Y, quinones, naphthols, N‐heterocyclic carbenes, carbazoles, pyrylium salts, etc.), without need photocatalysts. detailed mechanisms these photo‐catalyzed/promoted reactions also highlighted deeply. And we hope this will be helpful researchers interested promising field photocatalyzed transformations. magnified image

Language: Английский

Citations

51

Divergent electrosynthesis of 3-iodoindoles and indoles from 2-ethynylanilines under ambient and aqueous conditions DOI
Binbin Huang, Guiling Chen, Haoxiang Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3515 - 3521

Published: Jan. 1, 2023

A mild and simple electrochemical system has been developed for the efficient cyclization of 2-ethynylanilines to selectively access 3-iodoindoles or indoles.

Language: Английский

Citations

17

Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N─N chiral indoles DOI Creative Commons
Jinlei Wang, Deng Pan, Fen Wang

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(19)

Published: May 10, 2024

Atropisomeric indoles defined by a N─N axis are an important class of heterocycles in synthetic and medicinal chemistry material sciences. However, they remain heavily underexplored due to limited methods challenging stereocontrol over the short bonds. Here, we report highly atroposelective access axially chiral via asymmetric Larock reaction. This protocol leveraged powerful role phosphoramidite ligand attenuate common dissociation original reaction, forming with excellent functional group tolerance high enantioselectivity palladium-catalyzed intermolecular annulation between readily available o -iodoaniline alkynes. The multifunctionality prepared allowed diverse post-coupling transformations, affording broad array functionalized indoles. Experimental computational studies have been conducted explore reaction mechanism, elucidating enantio-determining rate-limiting steps.

Language: Английский

Citations

8

Indole: A promising scaffold for the discovery and development of potential anti-tubercular agents DOI Creative Commons
Nilesh Gajanan Bajad, Sudhir Kumar Singh, Sushil Kumar Singh

et al.

Current Research in Pharmacology and Drug Discovery, Journal Year: 2022, Volume and Issue: 3, P. 100119 - 100119

Published: Jan. 1, 2022

Indole-containing small molecules have been reported to diverse pharmacological activities. The aromatic heterocyclic scaffold, which resembles various protein structures, has received attention from organic and medicinal chemists. Exploration of indole derivatives in drug discovery rapidly yielded a vast array biologically active compounds with broad therapeutic potential. Nature is the major source scaffolds, but classical advanced synthesis methods for indoles also reported. One-pot widely considered an efficient approach synthetic chemistry used synthesize some compounds. rapid emergence drug-resistant tuberculosis challenge be addressed. Identifying novel targets candidates therefore crucial. Researchers extensively explored as potential anti-tubercular agents or drugs. Indole scaffolds containing non-covalent (decaprenylphosphoryl-β-D-ribose2'-epimerase) DprE1 inhibitor 1,4-azaindole currently clinical trials treat

Language: Английский

Citations

26

Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp2-Csp cross-coupling DOI Creative Commons
Fen Zhao, Mehdi Abdellaoui,

Wided Hagui

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: April 28, 2022

Abstract Photosensitization of organogold intermediates is an emerging field in catalysis. In this context, access to 2,3-disubstituted indoles from o -alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation the absence exogenous photocatalyst was uncovered. A wide scope process observed. Of note, 2-iodo-ynamides can be used as electrophiles cross-coupling reaction. The resulting N lend themselves post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converge on fact that potassium sulfonyl amide generates emissive aggregates reaction medium. Static quenching these by vinylgold(I) intermediate yields excited state latter, which react with electrophile oxidative addition reductive elimination forge key C-C bond. This reactant-induced photoactivation opens rich perspectives reactions.

Language: Английский

Citations

23

Indole frameworks via transition-metal-free annulation: a current perspective DOI
Suven Das

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(29), P. 13729 - 13775

Published: Jan. 1, 2023

The present review summarizes recent (2019–mid-2023) efforts towards the construction of indole core via transition-metal-free methods.

Language: Английский

Citations

10

Electrochemical selenocyclization of 2-ethynylanilines with diselenides: facile and efficient access to 3-selenylindoles DOI
Mingyu Zhang,

Zhenyu Luo,

Xinye Tang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(44), P. 8918 - 8923

Published: Jan. 1, 2023

An efficient electrochemical selenocyclization strategy for the synthesis of 3-selenylindoles from 2-ethynylanilines and diselenides has been developed in simple tube- or beaker-type undivided cells under ambient conditions. Notably, these sustainable transformations are completed within a short time with low equivalents charges, electrolytes, exhibiting broad substrate scope excellent functional group compatibility. Moreover, gram-scale electrosynthesis late-stage functionalization complex molecules further demonstrate practical synthetic potential this facile system.

Language: Английский

Citations

10

Organic and Inorganic Corrosion Inhibitors DOI
Goncagül Serdaroğlu, Savaş Kaya

Published: Nov. 7, 2021

Organic and inorganic compounds are widely used as corrosion inhibitors. It is important to mention that most of the toxic non-environmental friendly; therefore, their current use inhibitors strictly inhibited because increasing ecological awareness strict environmental regulations. Most organic become effective by adsorbing on metallic surface. Adsorption mostly follows Langmuir adsorption isotherm model. Polar functional groups multiple bonds act centers during metal inhibitor interactions. Present chapter deals with comparison various aspects inhibition using

Language: Английский

Citations

22

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives DOI
José S. S. Neto, Gilson Zeni

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(6), P. 1282 - 1318

Published: April 1, 2021

Abstract This review is intended to highlight the most useful approaches for synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3 H ‐indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition‐metal catalyzed cyclization reactions alkynes nitrogen compounds. The methodologies carried out under metal‐free conditions will also be illustrated herein. cover data published mostly in past decade.

Language: Английский

Citations

19

Annulation of 2‐Alkynylanilines: The Versatile Chemical Compounds DOI
Vaezeh Fathi Vavsari,

Ali M. Nikbakht,

Saeed Balalaie

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(2)

Published: Jan. 5, 2022

Abstract 2‐Alkynylanilines as versatile building blocks have been widely applied for the construction of nitrogen atom‐containing heterocycles in organic synthesis. The focus this review is on application 2‐alkynylaniline and its derivatives metal‐catalyzed or metal‐free synthesis various including indoles, oxindoles, indazoles, benzisoxazoles, quinolines, benzoxazines, benzothiazines, quinazolines, cinnolines, seven‐ eight‐membered heterocycles.

Language: Английский

Citations

11