Selective synthesis of pyridazin-fused chromones and 3-pyridazinyl chromones through intermolecular chromone annulation of o-hydroxyphenylenaminones with aryldiazonium salts

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3906 - 3912

Published: Jan. 1, 2024

A chemodivergent and skeleton-controllable annulation reactions of readily available o -HPEs aryldiazonium salts was described for the synthesis highly functionalized pyridazine-fused chromones with high antiviral activity higher safety.

Language: Английский

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I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

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Divergent Synthesis of 2-Chromonyl-3-hydrazono-chromones and 2-Alkoxy-3-hydrazono-chromones through Switchable Annulation Reactions of o-Hydroxyphenylenaminones with Aryldiazonium Salts

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 4980 - 4985

Published: June 4, 2024

An unprecedented selective chromone annulation reaction controlled by solvent for the divergent synthesis of two types 2,3-disubstituted skeletons has been developed. A variety 2-chromonyl-3-hydrazono-chromones and 2-alkoxy-3-hydrazono-chromones were constructed efficiently from readily available

Language: Английский

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Electrochemical C-H Halogenations of Enaminones and Electron-Rich Arenes with Sodium Halide (NaX) as Halogen Source for the Synthesis of 3-Halochromones and Haloarenes

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(17), P. 12378 - 12385

Published: Aug. 16, 2021

Without employing an external oxidant, the simple synthesis of 3-halochromones and various halogenated electron-rich arenes has been realized with electrode oxidation by simplest sodium halide (NaX, X = Cl, Br, I) as halogen source. This electrochemical method is advantageous for mild room temperature operation, environmental friendliness well broad substrate scope in both C–H bond donor source components.

Language: Английский

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Metal-free C(sp2)-H perfluoroalkylsulfonylation and configuration inversion: Stereoselective synthesis of α-perfluoroalkylsulfonyl E-enaminones

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 32(11), P. 3514 - 3517

Published: April 28, 2021

Language: Английский

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Visible-Light-Driven Multicomponent Cyclization by Trapping a 1,3-Vinylimine Ion Intermediate: A Direct Approach to Pyrimido[1,2-b]indazole Derivatives

Organic Letters, Journal Year: 2021, Volume and Issue: 23(21), P. 8343 - 8347

Published: Oct. 12, 2021

Here we develop a novel visible-light-driven three-component cyclization by trapping an 1,3-vinylimine ion intermediate for the direct synthesis of pyrimido[1,2-b]indazole derivatives from bromodifluoroacetic acid derivatives, enaminones, and 3-aminoindazoles under mild conditions. Notably, robust methodology provides valuable opportunity introduction aliphatic substituents enables good compatibility complex bioactive molecules. Furthermore, this is first example photoinduced multicomponent reaction employing as C1-synthon.

Language: Английский

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Transition‐Metal‐Free C(sp²)‐H Dithiocarbamation and Chromone Annulation Cascade for 3‐Dithiocarbamyl Chromone Synthesis

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(20), P. 4811 - 4816

Published: Aug. 26, 2021

Abstract The transition‐metal‐free synthesis of 3‐dithiocarbamyl chromones by reacting o ‐hydroxyphenylenaminones with thiurams in the presence KIO 3 and TEMPO is reported. In addition, synthesized herein have been successfully utilized as starting materials pyrimidines 3‐(benzylthio)chromones via featured chromone ring opening C−S bond cleavage, respectively. magnified image

Language: Английский

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Photoredox-Catalyzed Cascade of o-Hydroxyarylenaminones to Access 3-Aminated Chromones

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(2), P. 1477 - 1484

Published: Jan. 11, 2022

Reported herein is a photoredox-catalyzed amination of o-hydroxyarylenaminones with tert-butyl ((perfluoropyridin-4-yl)oxy)carbamate, versatile amidyl-radical precursor developed in our laboratory. This work establishes new cascade pathway for the assembly range 3-aminochromones under mild conditions. Downstream transformations obtained to construct diverse amino pyrimidines greatly broaden applications this photocatalyzed protocol.

Language: Английский

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Progress in the Study of α-Functionalization of Enaminone

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(2), P. 602 - 602

Published: Jan. 1, 2023

烯胺酮是一类非常重要的有机合成砌块, 具有易获得、储存方便、反应多样性等优点. 更重要的是, 烯胺酮是许 多杂环化合物的重要前体.最近

Language: Английский

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I₂-DMSO mediated dual α,β-C(sp²)–H functionalization/bicyclization of o-hydroxyphenyl enaminones to construct C2,C3-disubstituted chromone derivatives: chromeno[2,3-b]pyrrol-4(1H)-ones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4843 - 4847

Published: Jan. 1, 2023

An unprecedented dual α,β-C(sp 2 )–H functionalization/bicyclization strategy of o -hydroxyphenyl enaminones for the preparation chromeno[2,3- b ]pyrrol-4(1 H )-ones has been established.

Language: Английский

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