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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Direct Functionalization of para‐Quinones: A Historical Review and New Perspectives

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(27)

Published: May 21, 2024

Abstract The direct functionalization of quinones has always fascinated research communities due to their biological and redox activities subsequent application. Quinone motifs play a vital role as precursors for many bioactive compounds materials; hence, ingenious methodologies have been elaborated exploring these units. A significant part the synthetic strategies towards functionalized achieved by installing substituents on hydroquinones, phenols, or quinone itself different oxidative coupling reactions via radical pathways with without utilization metal catalysts. simple C−H bond remains challenging inherited electronic nature high dissociation energy. This review article summarizes recent advancement made through quinones. Our primary focus will be approaches mechanistic that appeared in last two decades, along short historical importance family.

Language: Английский

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Three-Component Reaction for the Synthesis of Spiro-Heterocycles from Isatins, Substituted Ureas, and Cyclic Ketones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3441 - 3452

Published: Feb. 20, 2024

We reported an efficient three-component reaction to access new spiro heterocycles through the annulation reactions of isatins, substituted ureas, and cyclic ketones under normal laboratory conditions, which is another example isatins being used build compounds by ring-opening recyclization processes. The wide range substrates, simple operation, experimental high yields make approach practical value.

Language: Английский

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Synthesis of Polycyclic Heteroarenes via Rh(III)-Catalyzed Twofold C-H Activation of 3-Aryl-2H-benzo[b][1,4]oxazines and Annulation with α-Diazo-β-ketoesters

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 14, 2025

An efficient Rh(III)-catalyzed annulation between 3-aryl-2H-benzo[b][1,4]oxazines and α-diazo-β-ketoesters was developed, affording a series of polycyclic heteroarenes in moderate to excellent yields with good functional group compatibility. The procedure featured high efficiency, redox neutrality, twofold ortho-C-H activation, dual [4 + 2] annulation. Moreover, several important intermediates products have been isolated as powerful evidence for the proposed reaction mechanism.

Language: Английский

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One-pot three-component synthesis of azaspirononatriene derivatives

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: April 30, 2025

The present investigation has introduced a new class of isocyanide/acetylene-based multicomponent reactions (IAMCRs). These are robust technique for efficiently synthesizing intricate spiro architectures through zwitterionic adduct. coupling reaction between the "in situ" generated dipoles isocyanide-acetylenic ester adducts and 3-alkyl-4-arylidene-isoxazol-5(4H)-one derivative presents highly effective synthetic pathway obtaining novel 1-oxo-2-oxa-3-azaspiro[4.4]nona-3,6,8-triene heterocycles. broad range substrates, standard experimental conditions, straightforward procedure, impressive yields make our catalyst-free three-component approach practical green, as it remarkably offers step-, time- cost-effectiveness based on green metrics.

Language: Английский

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Discovery of novel benzo[b][1,4]oxazine derivatives as ferroptosis inhibitors

Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: 156, P. 108201 - 108201

Published: Jan. 24, 2025

Language: Английский

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Straightforward Access to Free β^2,3,3‐Amino Acids through One Pot C‐H Activation/C−C Cleavage

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(18)

Published: Jan. 18, 2024

The first synthesis of unnatural β

Language: Английский

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Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(18), P. 8243 - 8276

Published: Jan. 1, 2024

The present review summarizes the recent advances (2018–2023) in stereoselective annulation involving p -benzoquinones for construction of fused, spiro and bridged/cage frameworks.

Language: Английский

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Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2223 - 2223

Published: Jan. 1, 2024

Language: Английский

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Synthesis of spiropyrans via Ru(ii)-catalyzed coupling of 3-aryl-2H-benzo[b][1,4]oxazines with benzoquinones

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(5), P. 998 - 1009

Published: Dec. 26, 2023

An efficient Ru( ii )-catalyzed C–H activation-based spiroannulation of benzoxazines with easily available benzoquinone and N -sulfonyl quinone monoimine has been realized, providing a straightforward strategy to access NH-containing spiropyrans.

Language: Английский

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