Novel Metal-Free Synthesis of 3-Substituted Isocoumarins and Evaluation of Their Fluorescence Properties for Potential Applications DOI Creative Commons
Mei Sun, Chongyang Zeng, Lu-Lu Bu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2449 - 2449

Published: May 23, 2024

A novel metal-free synthesis of 3-substituted isocoumarins through a sequential O-acylation/Wittig reaction has been established. The readily accessible (2-carboxybenzyl)-triphenylphosphonium bromide and diverse chlorides produced various 1H-isochromen-1-one in the presence triethylamine, employing O-acylation an intramolecular Wittig acid anhydride. Reactions using these facile conditions have exhibited high functional group tolerance excellent yields (up to 90%). Moreover, fluorescence properties isocoumarin derivatives were evaluated at theoretical experimental levels determine their potential application fluorescent materials. These good photoluminescence THF with large Stokes shift absolute quantum yield up 14%.

Language: Английский

Cascade Oxypalladation/1,3-Palladium Shift to Access Cyclopentene-Fused Isocoumarins DOI

Vaibhav B. Patil,

G. Raghu Ramudu,

Rambabu Chegondi

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6353 - 6358

Published: July 23, 2024

Fused isocoumarins are frequently found in several natural products and pharmaceuticals. Herein, a cascade annulation of 2-alkynylbenzoate-tethered cyclic 1,3-diones via sequential

Language: Английский

Citations

2
Polyfluorinated benzoic acids as promising reagents for organic synthesis and medicinal chemistry DOI
Evgeny V. Shchegolkov, Yanina V. Burgart,

Irina V. Shchur

et al.

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(8), P. RCR5131 - RCR5131

Published: Aug. 1, 2024

Polyfluoroaromatic compounds occupy a special place in organic synthesis due to wide range of their chemical transformations and unique biological properties. The introduction the carboxyl function into polyfluoroarenes allows further diversification chemistry these compounds. This review summarizes data on polyfluorobenzoic acids, including derivatives polyfluorosalicylic acids. reactions esterification, amidation, reduction, decarboxylation, metal-catalyzed decarboxylative cross-coupling, C–H functionalization, reductive defluorination, nucleophilic aromatic substitution, heterocyclization complex formation are considered. Reactivity features polyfluorobenzoates comparison non-fluorinated counterparts highlighted. potential for practical applications acid derivatives, primarily as biologically active compounds, is presented. <br> Bibliography includes 300 references.

Language: Английский

Citations

1
Asymmetric Total Synthesis of Naturally Occurring (R)-2′-Methoxydihydroartemidin, (R)-(E)-3′-Hydroxyartemidin, and Its Structural Congeners: Method Optimization and Mechanistic Analysis DOI
Swagata Das, Sayan Paul,

K. Mandal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15764 - 15776

Published: Oct. 18, 2024

Asymmetric total synthesis of naturally occurring 3-substituted isocoumarins, 2′-methoxydihydroartemidin, (E)-3′-hydroxyartemidin, and two structural congeners is reported in this article. Enantiopure 3-alkylisocoumarin core present those target molecules was accessed through an atom-economical regiodefined 6-endo-dig cyclization from properly substituted 2-halobenzoic acids chiral terminal alkynes ligand-free Cu(I) catalysis. A detailed mechanistic investigation carried out control experiments, density functional theory (DFT) analysis reveals that solvent directed a non-Sonogashira pathway direct insertion alkyne way operating. The synthesized 3-alkylisocoumarins are synthetically manipulated into various small molecular entities.

Language: Английский

Citations

1
Ru(II)-Catalyzed Decarboxylative (4 + 2)-Annulation of Benzoic Acids and Benzamides with Propargyl Cyclic Carbonates DOI

Debasish Jana,

Geetanjali S. Sontakke, Chandra M. R. Volla

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7590 - 7595

Published: Sept. 3, 2024

Propargyl cyclic carbonates have emerged as versatile precursors in synthetic chemistry. However, their reactivity has so far been limited to transition metal-catalyzed substitution and cyclization reactions. Herein, we illustrate the successful employment of propargyl coupling partners Ru(II)-catalyzed C-H annulation benzoic acids benzamides. This approach allowed us access a broad range biologically relevant isocoumarin isoquinolinone derivatives good excellent yields, utilizing bench-stable easily accessible precursors. Preliminary mechanistic studies indicated that metalation step is both reversible rate-determining reaction pathway. Furthermore, utility developed methodology illustrated by scale-up postfunctionalization experiments.

Language: Английский

Citations

0
Non-Kolbe Oxidation Driven Electrochemical C(sp2)-H Lactonization towards the Synthesis of Isocoumarins DOI
Chen Liu, Hongpeng Liu,

Gaoyuan Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6742 - 6747

Published: Jan. 1, 2024

A novel method for electrochemical C(sp 2 )–H lactonization was developed.

Language: Английский

Citations

0
Synthesis of 4-Fluoroisocoumarins by Copper-Catalyzed Annulation of 2-Halobenzoic Acids and 2-Fluoro-1,3-diketones DOI

Haruki Sakagami,

Akira Tsubouchi, Akio Saito

et al.

Journal of Fluorine Chemistry, Journal Year: 2024, Volume and Issue: 280, P. 110355 - 110355

Published: Oct. 9, 2024

Language: Английский

Citations

0
Synthesis of diarylsulphide/diarylselenide embedded pyrazole-fused isocoumarins and isatin/ninhydrin hydrazones via acid catalyzed solvent and temperature controlled reactions DOI
Sayanwita Panja,

Arun Dhurey,

Animesh Pramanik

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Room temperature stirring of a mixture chalcogenated arylhydrazones and ninhydrin in dichloromethane (DCM) the presence acid leads to formation pyrazole-fused isocoumarins, substituted with diarylsulphide/diarylselenide moiety. On other hand, refluxing same protic polar solvent ethanol produces containing hydrazones. Further study reveals that, like ninhydrin, isatin can also generate corresponding hydrazones at C-3 position under similar reaction conditions.

Language: Английский

Citations

0
Novel Metal-Free Synthesis of 3-Substituted Isocoumarins and Evaluation of Their Fluorescence Properties for Potential Applications DOI Creative Commons
Mei Sun, Chongyang Zeng, Lu-Lu Bu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2449 - 2449

Published: May 23, 2024

A novel metal-free synthesis of 3-substituted isocoumarins through a sequential O-acylation/Wittig reaction has been established. The readily accessible (2-carboxybenzyl)-triphenylphosphonium bromide and diverse chlorides produced various 1H-isochromen-1-one in the presence triethylamine, employing O-acylation an intramolecular Wittig acid anhydride. Reactions using these facile conditions have exhibited high functional group tolerance excellent yields (up to 90%). Moreover, fluorescence properties isocoumarin derivatives were evaluated at theoretical experimental levels determine their potential application fluorescent materials. These good photoluminescence THF with large Stokes shift absolute quantum yield up 14%.

Language: Английский

Citations

0