Photoinduced Tandem C‐O Bond Reduction / Ketyl Radical Addition Reactions of α‐Keto‐N,O‐Acetals Enabled by Proton‐Coupled Electron Transfer DOI Creative Commons
Paul Seefeldt, L Edelmann,

Adrian Prudlik

et al.

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(8)

Published: March 12, 2024

Abstract The C10a‐acetoxylated tetrahydroazepino[1,2‐ a ]indole‐6,11‐diones are class of tricyclic oxindoles that feature an α‐keto‐ N , O ‐acetal substructure, rendering them highly susceptible to SET reduction followed by fragmentation. In protic medium, they undergo PCET‐assisted two‐step including interposed C−O bond cleavage can be initiated photocatalytically as well cathodic reduction, and which generates nucleophilic ketyl radicals. the presence acrylonitrile DIPEA additional reactants, photoinduced reaction unfolds tandem reduction/ketyl radical conjugate addition, furnish C10a‐reduced, C11‐cyanoethyl‐substituted azepino‐[1,2‐ ]indole derivatives with high stereoselectivity.

Language: Английский

9-mesityl-10-methylacridinium perchlorate (Mes-Acr-Me+ClO4−) as a novel metal-free donor–acceptor (D–A) photocatalyst: visible-light-induced access to tetrahydrobenzo[b]pyran scaffolds through a single-electron transfer (SET) pathway DOI
Farzaneh Mohamadpour, Hesam Kamyab,

Shreeshivadasan Chelliapan

et al.

Research on Chemical Intermediates, Journal Year: 2024, Volume and Issue: 50(7), P. 2993 - 3007

Published: May 20, 2024

Language: Английский

Citations

2

Dual-Role of Thiourea for Synthesis of Copper Sulfide Decorated on Reduced Graphene Oxide/Graphitic Carbon Nitride for Advanced Photocatalysis DOI
Adi Darmawan, Hasan Muhtar, Desi Nur Pratiwi

et al.

Journal of Alloys and Compounds, Journal Year: 2024, Volume and Issue: unknown, P. 178008 - 178008

Published: Dec. 1, 2024

Language: Английский

Citations

2

An efficient, magnetically separable Fe 3 O 4 /HAp nanocomposite catalyzed one-pot synthesis of 5-alkoxycarbonyl-6-methyl-4-aryl-3,4-dihydropyrimidin-2(1H)-one derivatives DOI

Parthiban Devendiran,

Madhan Kuppusamy

Synthetic Communications, Journal Year: 2023, Volume and Issue: 53(22), P. 1918 - 1934

Published: Sept. 7, 2023

This article describes the synthesis of iron oxide/hydroxyapatite (Fe3O4/HAp) nanocomposite by hydrothermal method and utilization Fe3O4/HAp as a competent, reusable, magnetically separable nano-composite catalyst for one-pot 3,4-dihydropyrimidin-2(1H)-one derivatives cyclo-condensation dicarbonyl compound, aryl-aldehydes (thio)urea in EtOH:H2O (1:1, v/v) an eco-safe solvent. The nano-catalyst was characterized spectral analytical techniques such FT-IR, SEM, XRD, EDX VSM. advantage this procedure includes excellent product yield shorter time, simple workup procedure, reusability catalyst, avoidance volatile organic solvent, strong mineral acid.

Language: Английский

Citations

6

Catalytic role in Biginelli reaction: Synthesis and biological property studies of 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines DOI

Vinuta Kamat,

Dinesh S. Reddy,

Amit Kumar

et al.

Archiv der Pharmazie, Journal Year: 2023, Volume and Issue: 356(6)

Published: March 10, 2023

Abstract The Biginelli reaction has received significant consideration in recent years due to its easily accessible aldehyde, urea/thiourea, and active methylene compounds. When it comes pharmacological applications, the end‐products, 2‐oxo‐1,2,3,4‐tetrahydropyrimidines, are vital applications. Due ease of carrying out reaction, offers a number exciting prospects various fields. Catalysts, however, play an essential role Biginelli's reaction. In absence catalyst, is difficult form products with good yield. Many catalysts have been used search efficientmethodologies, including biocatalysts, Brønsted/Lewis acids, heterogeneous catalysts, organocatalysts, so on. Nanocatalysts currently being applied improve environmental profile as well speed up process. This review describes catalytic application 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines. study provides information that will facilitate development newer methods for by academics industrialists. It also broad scope drug design strategies, which may enable novel highly effective bioactive molecules.

Language: Английский

Citations

4

Synergistic effects of covalently coupled eosin‐Y with Ben‐graphitic carbon nitride framework for improved photocatalytic activity in solar light‐driven Biginelli product generation and NADH regeneration DOI

Anurag Prajapati,

Rajesh K. Yadav,

Rehana Shahin

et al.

Photochemistry and Photobiology, Journal Year: 2024, Volume and Issue: 100(6), P. 1773 - 1786

Published: June 28, 2024

Elevated global pollution level is the prime reason that contributes to onset of various harmful health diseases. The products Biginelli reaction are enormously used in pharmaceutical industry as they have antiviral, antibacterial, and calcium channel modulation abilities. This work reports a novel eosin Y sensitized boron graphitic carbon nitride (EY-B

Language: Английский

Citations

1

Scalable and green juglone synthesis via heterogeneous photocatalysis in a photomicroreactor DOI
Mohsin Pasha, Y. Andrew Wang,

You Ma

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(19), P. 5755 - 5763

Published: Jan. 1, 2024

A green and scalable heterogeneous photocatalysis platform is efficiently established for multigram juglone production using photomicroreactors, which are at the forefront of sustainable flow chemistry.

Language: Английский

Citations

1

Isonitriles as Alkyl Radical Precursors in Visible-Light Mediated Hydro– and Deuterodeamination Reactions DOI Creative Commons

Irene Quiros,

M. D. Martı́n, Miguel Gomez‐Mendoza

et al.

Published: Nov. 20, 2023

Herein, we report the use of isonitriles as alkyl radical precursors in light-mediated hydro- and deuterodeamination reactions. The reaction is scalable, shows broad functional group compatibility potential to be used late-stage functionalization. Importantly, method general for Cα-1º, Cα-2º Cα-3º isonitriles. For most examples, high yields were obtained through direct visible-light irradiation isonitrile presence a silyl precursor. Interestingly, an organic photocatalyst (4CzIPN) dramatic acceleration was observed. In depth mechanistic studies using UV-vis absorption, steady-state time-resolved photoluminescence, transient absorption spectroscopy suggest that excited state 4CzIPN able sensitize single electron transfer.

Language: Английский

Citations

3

Isonitriles as Alkyl Radical Precursors in Visible Light Mediated Hydro‐ and Deuterodeamination Reactions** DOI Creative Commons
Irene Quirós, María Martín, Miguel Gomez‐Mendoza

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(7)

Published: Dec. 27, 2023

Abstract Herein, we report the use of isonitriles as alkyl radical precursors in light‐mediated hydro‐ and deuterodeamination reactions. The reaction is scalable, shows broad functional group compatibility potential to be used late‐stage functionalization. Importantly, method general for C α ‐primary, ‐secondary ‐tertiary isonitriles. For most examples, high yields were obtained through direct visible‐light irradiation isonitrile presence a silyl precursor. Interestingly, an organic photocatalyst (4CzIPN) dramatic acceleration was observed. In‐depth mechanistic studies using UV/Vis absorption, steady‐state time‐resolved photoluminescence, transient absorption spectroscopy suggest that excited state 4CzIPN can engage single‐electron transfer with isonitrile.

Language: Английский

Citations

1

Acridine Yellow G: A Photo-induced Electron Transfer Photocatalyst for the Radical Synthesis of Pyrano[2,3- d ]pyrimidines in an Aqueous Medium DOI
Farzaneh Mohamadpour

Organic Preparations and Procedures International, Journal Year: 2024, Volume and Issue: 56(5), P. 419 - 428

Published: Feb. 7, 2024

Language: Английский

Citations

0

Photoinduced Tandem C‐O Bond Reduction / Ketyl Radical Addition Reactions of α‐Keto‐N,O‐Acetals Enabled by Proton‐Coupled Electron Transfer DOI Creative Commons
Paul Seefeldt, L Edelmann,

Adrian Prudlik

et al.

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(8)

Published: March 12, 2024

Abstract The C10a‐acetoxylated tetrahydroazepino[1,2‐ a ]indole‐6,11‐diones are class of tricyclic oxindoles that feature an α‐keto‐ N , O ‐acetal substructure, rendering them highly susceptible to SET reduction followed by fragmentation. In protic medium, they undergo PCET‐assisted two‐step including interposed C−O bond cleavage can be initiated photocatalytically as well cathodic reduction, and which generates nucleophilic ketyl radicals. the presence acrylonitrile DIPEA additional reactants, photoinduced reaction unfolds tandem reduction/ketyl radical conjugate addition, furnish C10a‐reduced, C11‐cyanoethyl‐substituted azepino‐[1,2‐ ]indole derivatives with high stereoselectivity.

Language: Английский

Citations

0