Radical-mediated photoredox hydroarylation with thiosulfonate

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2767 - 2770

Published: Jan. 1, 2023

Radical-mediated photoredox hydroarylation reaction of unactivated alkenes using thiosulfonate compounds as key radical precursors to synthesize pyridyquinazolinone and pyrroloquinazolinone derivatives is described.

Language: Английский

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Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Language: Английский

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Synthesis of CF₃–Isoquinolinones and Imidazole-Fused CF₃–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10180 - 10196

Published: July 4, 2024

Presented herein are novel syntheses of CF

Language: Английский

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Recent advances in the synthesis of 2,3-fused quinazolinones

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(32), P. 6293 - 6313

Published: Jan. 1, 2022

As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.

Language: Английский

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Recent Advances in Domino Synthesis of Fused Polycyclic N‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(24), P. 3751 - 3771

Published: Sept. 4, 2023

Comprehensive Summary Fused polycyclic N ‐heterocycles are very important scaffolds in biomedicinal chemistry and materials science. Intramolecular alkyne hydroamination is a powerful method for the construction of ‐heterocycles. In last two decades, copper‐catalyzed domino reactions based on intramolecular has emerged as robust strategy assembling various fused Great progress been achieved this area. This short review covers advances made synthesis from 2008 to 2023, will hopefully serve an inspiration towards exploration new versions transformation. The transformations introduced discussed five aspects according different key processes involved these reactions.

Language: Английский

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Copper‐Catalyzed Decarbonylative Cyclization of Isatins and Trifluoroacetimidohydrazides for the Synthesis of 2‐(5‐Trifluoromethyl‐1,2,4‐triazol‐3‐yl)anilines

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(5), P. 1044 - 1049

Published: Jan. 22, 2022

Abstract A copper‐catalyzed intramolecular decarbonylative cyclization reaction of isatins and trifluoroacetimidohydrazides for the synthesis 2‐(5‐trifluoromethyl‐1,2,4‐triazol‐3‐yl)aniline derivatives has been developed. This transformation proceeds through a cascade condensation, hydrolysis, decarboxylation, C−N bond formation sequence. The obtained 1,2,4‐triazole products bearing free amino group can be readily converted into other useful compounds. magnified image

Language: Английский

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NHPI/O₂‐Mediated Electrochemical Intermolecular Cyclization/Dehydrogenation for the Construction of Polycyclic Quinazolinones

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(13), P. 2248 - 2254

Published: May 27, 2023

Abstract Herein, an eco‐friendly and atom‐economical electrochemical methodology with isatins 1,2,3,4‐tetrahydroisoquinolines through NHPI/O 2 ‐mediated intermolecular oxidation/annulation is disclosed, leading to a variety of polycyclic quinazolinones in 46–82% yields. This oxidative cyclization proceeded transition metal‐ strong oxidant‐free conditions generated H CO as byproducts. Additionally, late‐stage functionalization broad substrate scope demonstrated the synthetic usefulness this protocol.

Language: Английский

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Copper-Catalyzed Domino Annulation of Isoselenocyanates: A Pathway to Structurally Diverse N, Se-Bis-Heterocyclic, and Fused Heterocyclic Compounds

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

Published: Jan. 10, 2025

A copper-catalyzed domino addition/cyclization reaction was developed to synthesize novel benzoselenazole-linked 1,2,3-triazole and tetracyclic fused 12H-benzo[4,5]selenazole[2,3-b]quinazolin-12-one derivatives from isoselenocyanates. This efficiently constructed multiple new chemical bonds in a single step, forming either four (one C–Se three C–N) or two bonds. The offers several key advantages, including mild conditions, broad substrate compatibility, straightforward safe operation. It presents method for synthesizing N, Se-containing polycyclic compounds, which have potential interest medicinal chemistry. Notably, some of the synthesized compounds exhibited anticancer activity with IC50 values below 20 μmol L–1 against T24 human bladder cancer cells.

Language: Английский

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Synthesis of Quinazolinone-Fused Tetrahydroisoquinolines and Related Polycyclic Scaffolds by Iodine-Mediated sp³ C–H Amination

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 1061 - 1074

Published: Jan. 11, 2023

An iodine-mediated intramolecular sp3 C-H amination reaction producing quinazolinone-fused polycyclic skeletons from 2-aminobenzamide precursors is reported. This does not use transition metals, has a broad substrate scope, and can be used on gram scale. Under the optimal conditions, variety of tetrahydroisoquinolines derivatives Rutaecarpine were synthesized readily accessible compounds. The proceeds well with crude derivatives, allowing for synthesis products simple 2-aminobenzoic acids without purification intermediates. Preliminary biological experiments have identified Cereblon (CRBN) inhibitory activity relevant anti-myeloma medicinal properties in some these products.

Language: Английский

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Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones

Molecules, Journal Year: 2024, Volume and Issue: 29(5), P. 997 - 997

Published: Feb. 25, 2024

The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple practical method the synthesis amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through carbamoyl-radical-triggered cascade cyclization N3-alkenyl-tethered quinazolinones. Notably, carbamoyl radical generated in situ from oxidative decarboxylative process oxamic acids presence (NH4)2S2O8.

Language: Английский

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