Development of a Continuous Flow Baldwin Rearrangement Process and Its Comparison to Traditional Batch Mode DOI Creative Commons
Arlene Bonner, Marcus Baumann

Organic Process Research & Development, Journal Year: 2023, Volume and Issue: 28(5), P. 1567 - 1575

Published: Sept. 11, 2023

A new and highly efficient continuous flow process is presented for the synthesis of aziridines via thermal Baldwin rearrangement. The was initially explored using traditional batch techniques but suffered from moderate yields, long reaction times, diastereoselectivities. Here we demonstrate that can be greatly improved upon its transfer to flow, which afforded aziridine targets in high short consistently diastereoselectivities, with high-throughput rendering multigram quantities product periods time. In addition, processing extended substrate scope including several examples had failed mode, thus demonstrating value this overlooked entry into valuable species.

Language: Английский

Syntheses, reactivity, and biological applications of coumarins DOI Creative Commons
Andrea Citarella, Serena Vittorio, Christian Dank

et al.

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Feb. 19, 2024

This comprehensive review, covering 2021-2023, explores the multifaceted chemical and pharmacological potential of coumarins, emphasizing their significance as versatile natural derivatives in medicinal chemistry. The synthesis functionalization coumarins have advanced with innovative strategies. enabled incorporation diverse functional fragments or construction supplementary cyclic architectures, thereby biological physico-chemical properties compounds obtained were enhanced. unique structure coumarine facilitates binding to various targets through hydrophobic interactions pi-stacking, hydrogen bonding, dipole-dipole interactions. Therefore, this important scaffold exhibits promising applications uncountable fields chemistry (e.g., neurodegenerative diseases, cancer, inflammation).

Language: Английский

Citations

21

Chiral CpxRhodium(III)‐Catalyzed Enantioselective Aziridination of Unactivated Terminal Alkenes DOI
Juanjuan Wang, Mupeng Luo, Yi‐Jie Gu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(12)

Published: Jan. 27, 2024

Chiral cyclopentadienyl-rhodium(III) Cp

Language: Английский

Citations

10

Preparation of a Novel Trimethoprim/Oxidized Pectin/Ti-MOF Nanoplymer as a Super Bioactive Agent DOI Creative Commons
Ahmad Irfan,

Munthar Kadhim Abosaoda,

Anjan Kumar

et al.

Journal of Inorganic and Organometallic Polymers and Materials, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 4, 2025

Language: Английский

Citations

1

Organic Dye-Sensitized Nitrene Generation: Intermolecular Aziridination of Unactivated Alkenes DOI Creative Commons
Dennis Dam,

Nathan R. Lagerweij,

Katharina M. Janmaat

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3251 - 3258

Published: Feb. 15, 2024

Aziridines are important structural motifs and intermediates, several synthetic strategies for the direct aziridination of alkenes have been introduced. However, many these require an excess activated alkene, suffer from competing side-reactions, limited functional group tolerance, or involve precious transition metal-based catalysts. Herein, we demonstrate by combining sulfonyl azides as a triplet nitrene source with catalytic amount organic dye functioning photosensitizer. We show how nature azide, in combination triplet-excited state energy photosensitizer, affects yield provide mechanistic rationale to account observed dependence reaction on azide reagents. The optimized conditions enable structurally diverse complex alkenes, carrying various groups, alkene limiting reagent.

Language: Английский

Citations

6

Visible light promoted synthesis of allenes DOI
Jitender Singh,

Barakha Saxena,

Anuj Sharma

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(18), P. 5143 - 5160

Published: Jan. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Language: Английский

Citations

3

Combined Synthetic, Spectroscopic, and Computational Insights Into a General Method for Photosensitized Alkene Aziridination DOI
Alana Rose Meyer, Mihai V. Popescu, Arindam Sau

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 12310 - 12317

Published: Aug. 2, 2024

Aziridines are important targets for synthetic chemistry, and many methods involving the aziridination of alkenes by olefins with nitrenes have been reported. In general, however, nitrene transfer reactions optimized a limited range precursors, synthesis structurally diverse aziridines featuring N-substituents requires application multiple varying reaction conditions. Herein, we report photocatalytic method that operates wide N-substituted precursors. A combination synthetic, spectroscopic, computational data is consistent mechanism generation triplet intermediates. The effectiveness 4DPAIPN as photocatalyst this process can be rationalized consequence its exceptionally long lifetime, rather than excited state energies or redox properties in isolation.

Language: Английский

Citations

3

A “phosphorus derivative” of aziridines: on the importance of ring strain energy and three heteropolar bonds in azaphosphiridines DOI
Antonio García Alcaraz, Alicia Rey Planells, Arturo Espinosa Ferao

et al.

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Compared to aziridines, azaphosphiridines, which formally result from the replacement of a carbon atom by phosphorus, have been much less studied. In this work, accurate values for one most prominent properties, ring strain energy (RSE), theoretically examined wide range azaphosphiridine derivatives. Strongly related aspects interest developing use azaphosphiridines in heteroatom and polymer chemistry are opening reactions polymerisations, latter facilitated their significantly high RSE. While methyl groups little influence on RSE, complexation with different metal moieties increases RSE all cases, an increase was also found upon oxidation corresponding P-oxides other σ5λ5-P The highest P-protonated azaphosphiridinium cation exocyclic double bonds. A correlation RSEs relaxed force constants endocyclic bonds AIM-derived parameters critical points, such as electron density, ρ(r), Lagrangian kinetic energy, G(r), found. relatively low barrier P-C bond cleavage via nucleophilic attack MeNH2 phosphorus points possibility ring-opening polymerisation.

Language: Английский

Citations

0

Reversible deprotonation as crucial step in bispidine copper-catalyzed aziridination reaction DOI Creative Commons

Thomas Josephy,

Markus Heiduk,

Tobias Saxl

et al.

Inorganica Chimica Acta, Journal Year: 2025, Volume and Issue: unknown, P. 122587 - 122587

Published: Feb. 1, 2025

Language: Английский

Citations

0

Phytotherapeutic Analysis of Chloroform-Based Fractions of Alstonia scholaris and Wrightia tinctoria Extracts Reveals Potent Anti-Psoriatic Activity: An In Vitro and In Vivo Study DOI Creative Commons

Mukti Ojha,

Nilanshu Manocha, Vinod Kumar

et al.

Pharmaceuticals, Journal Year: 2025, Volume and Issue: 18(3), P. 304 - 304

Published: Feb. 22, 2025

Background/Objectives: Psoriasis, a prevalent dermatological disorder, poses therapeutic challenges due to limited effective treatments or adverse side-effects. Traditional medicinal plants like Alstonia scholaris and Wrightia tinctoria, historically used in Ayurvedic Siddha practices, show potential treating inflammatory skin diseases. This study aims explore their vitro vivo anti-psoriatic properties develop safer more therapies. Methods: Chloroform:methanol fractions from ethanol extracts of tinctoria were evaluated for activity. In assays using HaCaT cells assessed cell viability, apoptosis, markers. studies utilized an IMQ-induced psoriasis mouse model, evaluating lesions, histopathology, cytokine profiles. Results: Chloroform significantly reduced viability induced apoptosis. They also dose-dependently downregulated IL-8 RANTES levels. vivo, these inflammation, edema, scores. Histopathological analysis showed decreased epidermal thickness dermal inflammation. Key biomarkers IL-17 IL-23 reduced. Conclusions: demonstrated potent effects vivo. These findings support as novel phytotherapeutic agents managing psoriasis, offering promise further development clinical application.

Language: Английский

Citations

0

Recent advances in the application of contiguously functionalized aziridines for the synthesis of pharmaceutical precursors via regioselective ring-opening reactions DOI
Huimyoung Byeon, Hyun‐Joon Ha, Jung Woon Yang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 576, P. 114943 - 114943

Published: Feb. 26, 2025

Language: Английский

Citations

0