Study on 1,4-hydride shift triggered spirocyclization of arylidene imidazolones: substituent control on formation of indane or tetrahydrobenzazepine systems

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(1), P. 18 - 21

Published: Jan. 1, 2025

Language: Английский

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HFIP-mediated three-component imidization of electron-rich arenes with in situ formed spiroindolenines for facile construction of 2-arylspiroindolenines

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(6), P. 1696 - 1702

Published: Jan. 1, 2022

The three-component reaction of o -aminobenzaldehydes with 5-hydroxyindole and electron-rich arenes has been achieved through HFIP-mediated cascade hydride transfer/dearomative cyclization/CDC-type imidization at room temperature under air.

Language: Английский

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Advances in chromone-based reactants in the ring opening and skeletal reconstruction reaction: access to skeletally diverse salicyloylbenzene/heterocycle derivatives

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(23), P. 4681 - 4698

Published: Jan. 1, 2022

Salicyloylbenzene/heterocycles are privileged scaffolds found in many natural products and bioactive molecules. Numerous useful approaches for the preparation of these have been developed recent years. Among approaches, chromone-based reactants demonstrated their importance synthesis salicyloylbenzene/heterocycle with structural complexity potential biological appeal. In this review, advances salicyloylbenzene/heterocycles summarized discussed according to which could be achieved one step via ring-opening skeletal reconstruction reactions. Both mechanisms applications corresponding organic medicinal chemistry also described.

Language: Английский

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The Cascade [1,5]-Hydride Shift/Intramolecular C(sp3)–H Activation: A Powerful Approach to the Construction of Spiro-Tetrahydroquinoline Skeleton

Frontiers in Chemistry, Journal Year: 2022, Volume and Issue: 10

Published: April 7, 2022

The direct functionalization of inert C–H bonds is regarded as one the most powerful strategies to form various chemical and construct complex structures. Although significant advancements have been witnessed in area transition metal-catalyzed bonds, several challenges, such utilization removal expensive metal complexes, limited substrate scope large-scale capacity, poor atom economy removing guiding groups coordinated metal, cannot fully fulfill high standard modern green chemistry nowadays. Over past decades, due its inherent advantage compared with a strategy, hydride shift activation that applies “ tert -amino effect” into common omnipresent C(sp 3 )–H adjacent -amines has attracted much attention from chemists. In particular, intramolecular [1,5]-hydride activation, mode, enables rapid effective production multifunctionally frameworks, especially spiro-tetrahydroquinoline derivatives, which are widely found biologically active natural products pharmaceuticals. great accomplishments achieved this promising field, rarely an updated review systematically summarized these important progresses despite scattered reports documented reviews. Hence, review, we will summarize advances cascade shift/intramolecular )-H perspective build skeleton, content categorized by structure type final containing pharmaceutical units. Besides, current limitations well future directions field also pointed out. We hope our could provide quick look offer some inspiration for research on strategy future.

Language: Английский

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Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(7), P. 1796 - 1802

Published: Jan. 1, 2023

An aromatization-driven hydride transfer-involved α-C(sp 3 )–H bond functionalization of the oxygen atom was developed. Easily prepared p -quinone methides were applied to initiate [1,5]-hydride transfer/cyclization for generating spirochromanes.

Language: Английский

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Divergent α-functionalization of cyclic amines via ring construction by molecular O₂ oxidized dearomatization and ring deconstruction by aromatization-driven C–C σ-bond cleavage

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(15), P. 5535 - 5541

Published: Jan. 1, 2021

An efficient approach to achieve the divergent α-C(sp³)–H functionalization of cyclic amines through an O₂ oxidized dearomatization/ring construction and aromatization-driven ring deconstruction/intermolecular strategy was developed.

Language: Английский

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Facile syntheses of tetrahydroquinolines and 1,2-dihydroquinolines via vinylogous cascade hydride transfer/cyclization

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(10), P. 2224 - 2231

Published: Jan. 1, 2021

The medicinally significant 3-monosubstituted tetrahydroquinolines and 1,2-dihydroquinolines were controllably constructed via redox-neutral vinylogous cascade condensation/[1,5]-hydride transfer/cyclization in EtOH.

Language: Английский

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A combination of polarity reversal, Diels–Alder cycloaddition and skeletal remodeling to access pyridine-fused nitrones

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(30), P. 4775 - 4778

Published: Jan. 1, 2022

An unprecedented cascade strategy consisting of polarity reversal, normal electron-demand Diels-Alder cycloaddition and skeletal remodeling was developed to construct novel pyridine-fused nitrones in up 82% yield. The key the success umpolung process, which transformed electron-deficient 3-nitropyridinium ring into a reactive, π-extended cyclic nitroalkene, serving as rarely reported hetero-diene participate cycloadditions.

Language: Английский

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Selective Reduction of Quinolinones Promoted by a SmI₂/H₂O/MeOH System

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(13), P. 8757 - 8763

Published: June 14, 2022

The selective reduction of quinolin-2(1H)-ones promoted by a SmI2/H2O/MeOH system is reported for the first time. reaction effectively carried out to afford 3,4-dihydroquinoline-2(1H)-ones under mild conditions in one-pot fashion with good excellent yields.

Language: Английский

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Lewis Acid-Catalyzed Chemodivergent and Regiospecific Reaction of Phenols with Quaternary Peroxyoxindoles

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14155 - 14167

Published: Oct. 21, 2022

The indium-catalyzed regiospecific coupling of substituted phenol derivatives and quaternary peroxyoxindoles for the synthesis C2 or C4 benzoxazin-3-one-substituted phenols via skeletal rearrangement is described. This reaction demonstrated with 17 examples good yields diverse aryl substituents. In contrast to reaction, Cu(OTf)2-catalyzed afforded 2-oxindole-substituted derivatives. catalytic generated various biologically important phenol-substituted 2-oxindole directly without any skeleton was 19 in high yield. regiospecificity pathways were explained support density functional theory (DFT).

Language: Английский

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