Construction of Oxygen‐ and Nitrogen‐based Heterocycles from p‐Quinone Methides

The Chemical Record, Год журнала: 2021, Номер 21(12), С. 4150 - 4173

Опубликована: Авг. 9, 2021

In the last few years, there has been an explosive growth in area of para-quinone methide (p-QM) chemistry. This boom is actually due to unique reactivity pattern p-QMs, and also their remarkable synthetic applications. fact, p-QMs serve as synthons for unsymmetrical diaryl- triarylmethanes, construction diverse range carbocycles heterocycles. a wide structurally complex heterocyclic frameworks could be accessed through transformations modified stable p-QMs. Therefore, main focus this review article cover recent advancements transition-metal, Lewis acid base-catalyzed/mediated p-quinone methides (p-QMs) oxygen- nitrogen-containing

Язык: Английский

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Unmasking the reverse reactivity of cyclic N-sulfonyl ketimines: multifaceted applications in organic synthesis

Chemical Communications, Год журнала: 2021, Номер 57(72), С. 9010 - 9028

Опубликована: Янв. 1, 2021

This feature article covers the recent status on reactivities of α-alkyl cyclic N -sulfonyl ketimines as resourceful nucleophiles, targeting fused carbo- and heterocycles, aza-arenes etc . In addition, mechanistic studies have been presented.

Язык: Английский

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Recent advances in the cyclization of para-quinone methides

Tetrahedron, Год журнала: 2023, Номер 148, С. 133655 - 133655

Опубликована: Окт. 9, 2023

Язык: Английский

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Tandem (2 + 2) Annulation/Retro-4π Electrocyclization/Imino-Nazarov Cyclization Reaction of p-Quinone Methides with Ynamides: Expeditious Construction of Functionalized Aminoindenes

Organic Letters, Год журнала: 2021, Номер 23(15), С. 5885 - 5890

Опубликована: Июль 19, 2021

A new tandem annulation of p-quinone methides (p-QMs) with ynamides is described. This cascade reaction features a unique combination (2 + 2) annulation, retro-4π electrocyclization, and imino-Nazarov cyclization, wherein vinyl (p-VQMs) as one the key intermediates have been identified chemically. Significantly, an unusual structural reconstruction p-QMs involving cleavage C5–C6 bond late-stage formation C4–C6 involved, leading to methodology development for construction functionalized aminoindenes.

Язык: Английский

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Substrate-Controlled Domino Reaction ofN-Sulfonyl Ketimines with 2-Aroyl-1-chlorocyclopropanecarboxylates: Access to Cyclopenta[c]chromenes and Benzo[f]cyclopenta[d][1,2]thiazepine Dioxides

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(9), С. 6721 - 6733

Опубликована: Апрель 12, 2021

An unprecedented substrate-controlled annulation method for the synthesis of fascinating classes angularly fused cyclopenta[c]chromenes and benzo[f]cyclopenta[d][1,2]thiazepine 5,5-dioxide derivatives in good to high chemical yields is reported. This Michael-initiated ring-expansion reaction would enable two C–C one C–O or C–N bonds by a judicious choice carbonucleophiles, either 4-alkyl 3-alkyl-substituted N-sulfonyl ketimines, respectively, with series donor–acceptor cyclopropane scaffolds as 4C sources promoted DBU. Moreover, this eco-friendly mild enough protect different kinds functionalities. Importantly, prepared fulvene were smoothly transformed into special class hexahydrocyclopenta[c]chromenes single cis–cis–cis–cis diastereomers excellent simple catalytic hydrogenation reaction.

Язык: Английский

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Recent Advances in Visible‐Light‐Driven Photocatalyzed γ‐Cyanoalkylation Reactions

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(7), С. 1595 - 1618

Опубликована: Май 22, 2021

Abstract Visible‐light‐induced photoredox‐catalyzed organic transformations through single‐electron‐transfer pathways have recently come to the limelight in modern chemistry. These innovative radical processes appear as ideal tactics for making a diverse set of pharmacologically and synthetically useful molecules under sustainable conditions. In this review, we summarize brief overview recent status C(sp3)−X (X=C, S, Se, B, F, Cl etc) cross‐coupling reactions cyclobutanone oxime esters surrogates γ‐cyanoalkyl radicals with various kinds acceptors using photocatalysts irradiated by visible light or natural sunlight. The efficiency metal‐salts (Ir, Ru, Cu, Pd metal‐free (eosin Y, rose Bengal, 4CzIPN, HE, PhPTZ, Mes−Acr+ were thoroughly examined above conversions. Furthermore, mechanism said has also been presented. Notably, described photocatalytic cycles would further bestow new mechanistic concept aiming variety cyanoalkylated scaffolds.

Язык: Английский

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Recent advances and future challenges in the synthesis of 2,4,6-triarylpyridines

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(38), С. 8184 - 8204

Опубликована: Янв. 1, 2021

The present review is focused on recent advances (2015–present) in the synthesis of 2,4,6-triarylpyridines (also known as Kröhnke pyridines).

Язык: Английский

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One-pot π-extension approach of iminoindoles-to-α-carbolines as blue-light emitters using the cooperative basic system

New Journal of Chemistry, Год журнала: 2024, Номер 48(32), С. 14163 - 14169

Опубликована: Янв. 1, 2024

Efficient access to α-carbolines was achieved via a domino reaction between iminoindoles and arylidene malononitriles using DABCO/NaHCO 3 as cooperative basic system. The synthesized scaffolds display blue emissions with good quantum yields.

Язык: Английский

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Five-membered cyclic sulfamidate imines: versatile scaffolds for organic synthesis

Organic & Biomolecular Chemistry, Год журнала: 2020, Номер 18(38), С. 7467 - 7484

Опубликована: Янв. 1, 2020

Five-membered ring cyclic sulfamidate imines (5H-1,2,3-oxathiazole 2,2-dioxides) have received increasing attention as useful precursors for the synthesis of many valuable heterocycles. This review highlights recent developments in this area.

Язык: Английский

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1,6-Aza-Michael addition of para-quinone methides with N-heterocycles catalyzed by Zn(OTf)2: A regioselective approach to N-diarylmethyl-substituted heterocycles

Tetrahedron, Год журнала: 2020, Номер 76(28-29), С. 131338 - 131338

Опубликована: Июнь 10, 2020

Язык: Английский

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