Ketones as strategic building blocks for the synthesis of natural product-inspired compounds

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(10), P. 4094 - 4120

Published: Jan. 1, 2022

This review explores and summarises synthetic methods that may be used to prepare heterocyclic ring systems from non-activated ketones, considers their potential value towards the synthesis of natural product-inspired compound collections.

Language: Английский

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Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis–Cyclization Reaction

The Journal of Organic Chemistry, Journal Year: 2015, Volume and Issue: 80(10), P. 5287 - 5295

Published: April 21, 2015

Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis substituted pyrroles. A series pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid procedurally simple also represent a facile entry to synthetically challenging 1,2,3-substituted value methodology is further corroborated by conversion pyrroles into 3-methyl-pyrrolines derivatization 3-methyl-substituent arising from reaction.

Language: Английский

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Hydrogen-Bond-Assisted Ru(III)-Catalyzed C–C Bond Activation in 1,3-Dicarbonyls: A Direct Route to Multi-Substituted Pyrroles

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Unprecedented CO-Cα bond cleavage of 1,3-dicarbonyls and enaminone, catalyzed by a well-defined Ru(III)-complex (1) featuring redox-active triamine ligand (L1) with free -NH2 arm, opening new route to accessing substituted pyrroles broad substrate scope functional group tolerance in good isolated yields via multicomponent coupling 1,3-dicarbonyls, amines, diol, is reported. The hydrogen bonding interaction offered 1 facilitates the formation critical reaction intermediates, favoring pyrroles.

Language: Английский

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Iridium‐Catalyzed Sustainable Access to Functionalized Julolidines through Hydrogen Autotransfer

ChemCatChem, Journal Year: 2015, Volume and Issue: 7(7), P. 1090 - 1096

Published: March 10, 2015

Abstract The straightforward and ecofriendly preparation of functionalized julolidines starting from tetrahydroquinoline, diols, aldehydes, for which water is produced as the only side product was investigated. To achieve this task, several well‐defined ruthenium iridium complexes including three new were prepared corresponding phosphine–sulfonates, phosphine–carboxylates, phosphine–phosphonates. first transformation involved in situ generation enaminoiminium intermediates, allowed formation through formal N,C(sp 2 )‐cyclization tetrahydroquinoline propane‐1,3‐diols. influence chelate acidity points out that [Cp*Ir III ]‐based catalysts (Cp*=C 5 Me ) featuring phosphine–carboxylate phosphine–sulfonate ligands suitable cyclization, whereas acidic phosphinophosphonate‐containing complex favored reduced N‐alkylated tetrahydroquinoline. We found substitution propane‐1,3‐diols crucial ions, accounts efficiency selectivity reaction. Applying another hydrogen autotransfer process, easily at C2 position.

Language: Английский

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Recent Progress in the Synthesis of Pyrroles

Current Organic Chemistry, Journal Year: 2020, Volume and Issue: 24(6), P. 622 - 657

Published: Feb. 28, 2020

: Pyrrole derivatives are nitrogen-containing heterocyclic compounds and widely distributed in a large number of natural non-natural compounds. These possess broad spectrum biological activities such as anti-infammatory, antiviral, antitumor, antifungal, antibacterial activities. Besides their activity, pyrrole have also been applied various areas dyes, conducting polymers, organic semiconductors. Due to wide range applicability, access this class has attracted intensive research interest. Various established synthetic methods Paal-Knorr, Huisgen, Hantzsch modified improved. In addition, numerous novel for synthesis discovered. This review will focus on considerable studies the pyrroles, which date back from 2014.

Language: Английский

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Synthesis of new bimetallic phosphate (Al/Ag3PO4) and study for its Catalytic performance in the synthesis of 1,2-dihydro-l-phenyl-3H-naphth [1,2-e]-[1,3] oxazin-3-one derivatives

Mediterranean Journal of Chemistry, Journal Year: 2021, Volume and Issue: 11(3), P. 215 - 215

Published: Aug. 9, 2021

<p>This work aims to prepare a new bimetallic phosphate catalyst using simple and effective method. This was ready for the first time by modification of Triple Super Phosphate (TSP) fertilizer with silver sulfate (AgSO₄), followed impregnation aluminum atoms nitrate (Al(NO₃)₃). The use Al/Ag₃PO₄, as heterogeneous in organic chemistry, offers new, efficient, green pathway synthesizing 1,2-dihydro-l-phenyl-3H-naphth[1,2-e]-[1,3]oxazin-3-one derivatives one-pot three-component cyclocondensation b-naphthol, aryl aldehyde, urea. structure morphology prepared were characterized spectroscopic methods such X-Ray Diffraction (XRD), Fourier Transform Infrared spectroscopy (FT-IR), dispersive X-ray spectrometry coupled scanning electron microscope (EDX-SEM). In addition, optimization reaction parameters carried out considering effect amount, temperature, solvent. procedure described herein allowed comfortable preparation oxazine excellent yields, short times, absence solvent.</p>

Language: Английский

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Polyethylene glycol (PEG‐400) Mediated One‐pot Green Synthesis of 4,7‐Dihydro‐2H‐pyrazolo[3,4‐b]pyridines Under Catalyst‐free Conditions

ChemistrySelect, Journal Year: 2020, Volume and Issue: 5(40), P. 12407 - 12410

Published: Oct. 23, 2020

Abstract Polyethylene glycol (PEG‐400) was proved a highly efficient and green solvent reaction medium for the synthesis of series novel 3,6‐dimethyl‐4,7‐dihydro‐2 H ‐pyrazolo[3,4‐ b ]pyridine derivatives with excellent yields by three‐component 1 ‐pyrazol‐3‐amino‐5‐methyl, various aromatic or heteroaromatic aldehydes chosen CH‐active compounds under catalyst‐free conditions via one‐pot strategy. This transformation is compatible broad diversity functional group tolerance. Rapid synthesis, mild conditions, high yields, no catalyst column chromatography, cost‐effectiveness are benefits this protocol.

Language: Английский

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Convenient synthesis of polysubstituted pyrroles and symmetrical and unsymmetrical bis-pyrroles catalyzed by H3PW12O40

Comptes Rendus Chimie, Journal Year: 2016, Volume and Issue: 19(3), P. 381 - 389

Published: Jan. 21, 2016

Language: Английский

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Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp³ C–H Bond Activation

ACS Omega, Journal Year: 2018, Volume and Issue: 3(4), P. 4289 - 4294

Published: April 16, 2018

The FDA-approved drug for the treatment of asthma, zafirlukast, is synthesized engaging multiple catalytic reactions including a new method construction 3-aroylindoles via oxidative cyclization. highlights include transition-metal and peroxide free C-H bond activation using stoichiometric amount sodium persulfate as an oxidizing agent in 3-aroylindole, avoiding transition metal, with over 28% overall yield. complete process has turnaround time 28 h to get target molecule starting from substituted aniline, practically no protecting groups.

Language: Английский

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PEG-400 as a recyclable solvent in the synthesis of β-arylthio-α,β-unsaturated esters, ketone and aldehyde under base and catalyst-free conditions

Journal of environmental chemical engineering, Journal Year: 2016, Volume and Issue: 4(2), P. 2004 - 2007

Published: March 16, 2016

Language: Английский

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