An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110784 - 110784

Опубликована: Дек. 1, 2024

Язык: Английский

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Controllable Molecular Editing of 2-Amino-N-substituted Benzamides: Site-selective Synthesis of 6-Selenylated N-Substituted 1,2,3-Benzotriazine-4(3H)-ones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 3, 2025

We present an efficient silver-catalyzed one-pot controllable molecular editing protocol for the transformation of 2-amino-N-substituted benzamides into 6-selenylated N-substituted 1,2,3-benzotriazine-4(3H)-ones under mild reaction conditions. This three-component strategy is achieved by building N-N/N═N/C-Se bonds, which provides a practical pathway preparation selenylated with broad substrate scope and good functional group tolerance, as well high site-selectivity. Mechanistic experiments suggest that this proceeds via intermolecular site-selective C-H selenylation readily available diselenides, followed annulation using AgNO3 nitrogen synthon.

Язык: Английский

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Eco-Friendly and Efficient Synthesis of 2-Hydroxy-3-Hydrazono-Chromones Through α,β-C(sp2)–H Bond Difunctionalization/Chromone Annulation Reaction of o-Hydroxyaryl Enaminones, Water, and Aryldiazonium Salts

Molecules, Год журнала: 2025, Номер 30(6), С. 1194 - 1194

Опубликована: Март 7, 2025

A novel, eco-friendly, and efficient method for constructing 2,3-disubstituted chromone skeletons from readily available water, o-hydroxyaryl enaminones (o-HPEs), aryldiazonium salts has been developed under mild reaction conditions. This α,β-C(sp2)–H bond difunctionalization/chromone annulation strategy is achieved by building two C(sp3)–O bonds a C(sp2)-N bond, which provides practical pathway the preparation of 2-hydroxy-3-hydrazono-chromones in moderate to excellent yields, enabling broad substrate scope good functional group tolerance, as well gram-scale synthesis. protocol offers valuable tool synthesizing diverse functionalized chromones with potential applications drug discovery industrial

Язык: Английский

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Water-Controlled Geminal Hydroxyphosphinoylation and Diphosphinoylation of Enaminones with H-Phosphine Oxides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 6, 2025

A water-controlled geminal phosphinoylation of enaminones with H-phosphine oxides has been established through AlCl3-mediated C-N bond cleavage in this work, which provides a novel strategy for accessing various hydroxy and diphosphinoyl products 3a 4a high yields. The transformation features excellent functional group tolerance, operational simplicity, atom economy, is amenable complex molecule skeletons. Preliminary mechanism studies suggest the conversion from to involve elimination hydroxyl group, water temperature plays critical role influencing reaction pathway product selectivity. This research significant value functionalization enaminones.

Язык: Английский

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I₂-Induced Umpolung: Synthesis of a 1,6-Dihydrofuro[3,2-b]pyrazolo[3,4-e][1,4]thiazine Skeleton via an Unconventional 1,4-Dithiane-2,5-diol Reaction Mode

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7891 - 7896

Опубликована: Сен. 6, 2024

In this paper, novel sulfur-containing 1,6-dihydrofuro[3,2-

Язык: Английский

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Divergent Assembly of Functionalized Pyrazolo[1,5‐a]pyridine Derivatives via [3+2] Cyclization of N‐Aminopyridinium Salts with Various Unsaturated Hydrocarbons

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 10, 2024

Comprehensive Summary Two reaction modes for metal‐free [3 + 2] cyclization of N ‐aminopyridinium derivatives with β ‐alkoxyvinyl trifluoromethylketones have been described through selective C—O or C—O/C—C bond cleavage. This strategy can also be extended to the enaminones and bromoalkynes. A broad range ‐aminopyridinium, ‐aminoquinolinium, ‐aminoisoquinolinium salts are well tolerated, enabling divergent synthesis trifluoroacylated, non‐substituted, acylated, brominated pyrazolo[1,5‐ a ]pyridine (62 examples).

Язык: Английский

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Transition-Metal Free Approaches to Access N-Heterocycles and Valuable Intermediates from Aryldiazonium Salts

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

Development of novel and efficient synthetic methods to achieve valuable N-heterocycles from aryldiazonium salts has been an important research area in organic chemistry for several decades.

Язык: Английский

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Zinc‐Catalysed [3+2] Cycloaddition of Enaminone with Tosylhydrazide to Synthesise 1H‐pyrazole via C–N and S–N Bond Cleavage

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 14, 2024

Abstract A novel and practical zinc‐catalysed synthesis of 1 H ‐pyrazole has been developed. The one‐pot protocol enables the cycloaddition enaminone tosylhydrazide via C−N S−N bond breaking process, leading to diverse mono‐substituted pyrazole derivatives in high yields. Moreover, easily accessible materials, broad substrate scope with excellent functional group tolerance, ease isolation open‐air conditions are key features present method.

Язык: Английский

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Divergent Sc(OTf)3‐Catalyzed Tandem Cyclization of o‐Hydroxyphenyl Enaminones with 1,3,5‐Triazinanes: Access to C3‐Aminomethyl Chromones and Tetrahydropyrimidines

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 9, 2024

Abstract A Sc(OTf) 3 ‐catalyzed tandem cyclization reaction of o ‐hydroxyphenyl enaminones with 1,3,5‐triazinanes has been developed to generate two distinct annulated products in moderate good yields, which is dominated by the electronic characteristics 1,3,5‐triazinanes. The 1,3,5‐triaryl‐1,3,5‐triazinane reacted as C−N synthon produce C3‐aminomethyl chromone, while 1,3,5‐trialkyl‐1,3,5‐triazinane acted C−N−C−N synthons deliver N , ‐dialkyl tetrahydropyrimidine a free hydroxyl group.

Язык: Английский

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NBS-Mediated C(sp2)-H Bond Chlorination of Enaminones: Using DCE as Chlorine Source

International Journal of Molecular Sciences, Год журнала: 2024, Номер 25(22), С. 12073 - 12073

Опубликована: Ноя. 10, 2024

Commercial DCE is excavated as both a "Cl" source and solvent for the vinyl C(sp

Язык: Английский

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