C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(12), P. 2324 - 2338

Published: Jan. 1, 2024

This review summarizes the most recent progress made in C–H bond activation-initiated spiroannulation reactions and their applications construction of structurally diverse biologically valuable spirocyclic scaffolds.

Language: Английский

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Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(15), P. 2916 - 2947

Published: Jan. 1, 2024

In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.

Language: Английский

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The solvent-controlled Rh(iii)-catalyzed switchable [4+2] annulation of 2-arylIndoles with iodonium ylides

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(41), P. 6140 - 6143

Published: Jan. 1, 2022

Highly selective and switchable [4+2] annulations of 2-arylindoles with iodonium ylides were achieved by performing solvent-controlled Rh(III)-catalyzed C-H activations. When using DCM as a solvent, the functionalization selectively delivered indolo[2,1-a]isoquinoline derivatives. In contrast, same catalytic system polar HFIP solvent predominately provided benzo[a]carbazole moieties.

Language: Английский

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Recent advances in transition-metal-catalyzed directed C–H alkenylation with maleimides

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(24), P. 4837 - 4845

Published: Jan. 1, 2022

Transition-metal-catalyzed directed C-H alkenylation with maleimides has attracted much attention in recent years, as maleimide core moieties are present various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important compounds including succinimides, pyrrolidines γ-lactams. The efficient chelation-assisted inert bond activation strategy provides straightforward access to a wide array of structurally diverse molecules containing units. This review describes the major progress mechanistic investigations on Heck-type reaction/cyclization organic until early 2022.

Language: Английский

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Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(43), P. 5862 - 5879

Published: Oct. 20, 2021

Abstract Maleimides and succinimides are all vital scaffolds in biological fields various natural products. Maleimide derivatives have been extensively used as coupling partners for organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, variety efficient chelation‐assisted strategies employed selective addition C−H bonds to maleimides giving succinimides, which also highly building blocks synthesis. This Review provides an overview research progress relating participated transition‐metal‐catalyzed group‐directed alkylation from 2012 2021. Significant advances this field were highlighted, diverse transition metal catalysts, substrates contained different directing groups, reaction mechanisms well synthetic applications systematically discussed. addition, limitations intractable issues need be solved future pointed out.

Language: Английский

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Copper(I)-Mediated Cascade Annulation via Dual C–H/C–H Activation: Access to Benzo[a]carbazolic AEEgens

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 16948 - 16964

Published: Nov. 16, 2021

A Cu(I)-mediated cascade cyclization/annulation of unprotected o-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation C–N and two C–C bonds to deliver fused benzo[a]carbazoles having free NH skeletons. annulated products display fluorescence emission the range 485–502 nm a large Stokes shift lifetime ∼17 ns. 3aa displays AEE behavior ethanol/hexane system possesses marigold-flower-like morphology at aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular depicts cell imaging applicability.

Language: Английский

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Iridium-Catalyzed Tandem Dehydrogenation/Hydroarylation Approach to Synthetically Versatile C2-Alkenyl N–H Indoles

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(5), P. 2872 - 2882

Published: Feb. 9, 2024

Readily available N-carbamoyl indolines can be converted into highly valuable 2-alkenyl and 2-alkyl indoles in a one-pot reaction, through an autotandem catalytic cascade promoted by iridium complex. The process entails dehydrogenation reaction initiated iridium-promoted C(sp3)–H activation, the addition of resulting indole to alkyne -or alkene-partner, spontaneous loss carbamoyl directing group. Interestingly, C2-alkenyl participate variety metal-catalyzed annulations C–H including formal [4 + 1] 2] cycloadditions, as well cross-dehydrogenative cyclizations, thus enabling divergent access collection functionally rich nitrogen-containing heterocycles.

Language: Английский

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Synthesis of spirosuccinimides via annulative cyclization between N-aryl indazolols and maleimides under rhodium(iii) catalysis

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(83), P. 10947 - 10950

Published: Jan. 1, 2021

The rhodium(III)-catalyzed spiroannulation reaction between N-aryl indazol-3-ols and maleimides is described herein. developed method showcased by the construction of spirosuccinimides using bioactive molecule-linked chemical probe-linked maleimides. Combined mechanistic investigations including determination an isolable rhodacycle complex aided elucidation a plausible mechanism.

Language: Английский

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Chemodivergent Synthesis of Indeno[1,2-b]indoles and Isoindolo[2,1-a]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(16), P. 10967 - 10981

Published: July 28, 2022

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3·2H2O selectively promoted an intramolecular C–H/C–H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while C–H/N–H could proceed via electrochemistry deliver isoindolo[2,1-a]indoles. Plausible mechanisms chemodivergent reactions were proposed.

Language: Английский

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Ru(II)-Catalyzed [4 + 2]-Annulation of 2-Alkenyl/Arylimidazoles with N-Substituted Maleimides and 1,4-Naphthoquinones: Access to Imidazo-Fused Polyheterocycles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2272 - 2282

Published: Feb. 2, 2024

Synthesis of imidazo-fused polyheterocyclic molecular frameworks, viz. imidazo[1,2-a]pyrrolo[3,4-e]pyridines, imidazo[2,1-a]pyrrolo[3,4-c]isoquinolines, and benzo[g]imidazo[1,2-a]quinoline-6,11-diones, has been achieved by the ruthenium(II)-catalyzed [4 + 2] C–H/N–H annulation 2-alkenyl/2-arylimidazoles with N-substituted maleimides 1,4-naphthoquinones. The developed protocol is operationally simple, exhibits broad substrate scope excellent functional group tolerance, provides desired products in moderate to good yields. mechanistic studies suggest that reaction involves formation a C–C bond through Ru-catalyzed C(sp2)–H activation followed intramolecular cyclization.

Language: Английский

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