Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
A facile one-pot synthesis of oxygen- and nitrogen-containing benzoheterocycles has been achieved through [4 + 1] annulation para -quinone methides, followed by an oxidation/elimination sequence.
Язык: Английский
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Янв. 3, 2025
A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6H-benzo[c]chromene scaffolds. Various 6H-benzo[c]chromenes were synthesized under mild conditions using easily accessible p-QMs and commercially available o-hydroxyarylboronic acids. One the chromenes has been ambiguously confirmed single-crystal XRD analysis. Interestingly, our could be transformed into valuable 6H-benzo[c]chromen-6-ones via oxidation.
Язык: Английский
Процитировано
2
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Март 4, 2025
The present study reveals the design and development of an N-heterocyclic carbene (NHC)-catalyzed intramolecular vinylogous Stetter reaction. This protocol enabled synthesis diverse phenanthrol derivatives naphthol-fused heterocycles in very good to excellent yields. success title reaction relies on biaryl aldehydes bearing p-quinone methide (p-QM) moiety that acts as a (1,6-conjugate) acceptor while aldehyde functional group serves acyl anion equivalent, generated situ from NHC-catalyzed umpolung. Salient features presented include atom efficiency, operational simplicity, broad substrate scope, large-scale synthesis, postsynthetic modifications.
Язык: Английский
Процитировано
1
Science China Chemistry, Год журнала: 2023, Номер 66(5), С. 1467 - 1473
Опубликована: Апрель 12, 2023
Язык: Английский
Процитировано
19
The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(10), С. 6730 - 6741
Опубликована: Май 12, 2022
Multicomponent synthesis of biologically relevant S-benzyl dithiocarbamates from para-quinone methides, amines, and carbon disulfide are described under catalyst additive-free conditions. The reactions proceeded at room temperature in a short span time with excellent yields. One the synthesized compounds, 3e showed considerable acetylcholinesterase (AChE) inhibitory (51.70 + 5.63% 20 μm) antioxidant (63.52 ± 1.15 activities.
Язык: Английский
Процитировано
28
Tetrahedron, Год журнала: 2023, Номер 148, С. 133655 - 133655
Опубликована: Окт. 9, 2023
Язык: Английский
Процитировано
15
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 2847 - 2857
Опубликована: Фев. 16, 2024
In recent years, the application of fluorinated alcohols as solvents, cosolvents, or additives has become important in modern organic synthesis. However, their potential efficient catalysts synthesis not been well-explored. this article, we report on development a one-pot sequential cascade reaction p-quinone methides with difluoroenoxysilanes using hexafluoroisopropanol catalyst. This allows for preparation multisubstituted oxa-spiro[4,5]cyclohexadienones. By 50 mol % 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP), proceeds smoothly to yield 1,6-conjugated products, which are then subjected oxidative dearomatization/hemiacetalization PhI(OAc)2. The overall process affords moderate high yields and excellent diastereoselectivities.
Язык: Английский
Процитировано
6
Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(12), С. 2504 - 2508
Опубликована: Янв. 1, 2023
KO t Bu mediated addition of sulfonylphthalides to p -quinone methides led the selective synthesis isochroman-1,4-diones and products. Furthermore, a few products were transformed into functionalized heterocyclic molecules.
Язык: Английский
Процитировано
13
Acta Chimica Sinica, Год журнала: 2023, Номер 81(7), С. 793 - 793
Опубликована: Янв. 1, 2023
o-Hydroxyphenyl substituted p-quinone methides (p-QMs) belong to a class of p-QMs with unique advantages.They not only maintain the high reactivity p-QMs, but also have more reactive and activation sites owing introduction hydroxyl group.Therefore, o-hydroxyphenyl wide applications in synthetic medicinal chemistry.The catalytic asymmetric 1,6-conjugate addition [4＋n] cycloaddition developed very rapidly recent years, which become efficient strategies for synthesis chiral oxygen-containing heterocycles arylmethanes potential bioactivity.This review summarizes reactions involving points out remaining challenges this research area, will open new window design type their involved reactions.
Язык: Английский
Процитировано
13
ChemistryEurope, Год журнала: 2023, Номер 1(1)
Опубликована: Май 3, 2023
Abstract The enantioselective α‐functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6‐additions to para‐quinone methides (21 examples, up 95 : 5 dr and 96 4 er) 1,4‐ additions methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 98 2 er). This nucleophilic organocatalysis approach gives access a range α‐functionalised α‐amino acid derivatives further transformations the activated ester group provide straightforward entry advanced amino acid‐based esters, amides thioesters.
Язык: Английский
Процитировано
11
Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(30), С. 6174 - 6179
Опубликована: Янв. 1, 2023
Simple irradiation of quinones and alkynes with blue light is sufficient to trigger [2 + 2] photocycloadditions giving rise either fused cyclobutenes or reactive para -quinone methides depending on the quinone structure.
Язык: Английский
Процитировано
11