One-Pot Three-Component Synthesis of Indolyl-4H-chromene-3-sulfonyl Fluoride: A Class of Important Pharmacophore

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3618 - 3628

Published: Feb. 15, 2024

A one-pot, sequential three-component reaction between salicylaldehyde, indole, and 2-bromoprop-2-ene-1-sulfonyl fluoride (BPESF) has been demonstrated for the synthesis of sulfonyl substituted 4H-chromene derivatives in moderate to excellent yields (45%–94%). This one-pot method features easily available starting materials, wide substrate scope, mild conditions, great efficiency.

Language: Английский

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Synthesis and Characterization of a Hercynite-Supported Copper(II) Complex Based on 1,10-Phenanthroline-5,6-dione and Acetylacetone Building Blocks and Its Catalytic Application in Annulation Reactions

Langmuir, Journal Year: 2024, Volume and Issue: 40(43), P. 22773 - 22786

Published: Oct. 18, 2024

In the present work, a novel Cu(II) complex containing 10-phenanthroline-5,6-dione (phen-dione) and acetylacetone (acac) was prepared via solid-phase synthesis on silica-modified hercynite magnetic nanoparticles (MNPs). The resulting structure underwent thorough structural analysis using diverse instrumental techniques. catalytic potential of synthesized successfully demonstrated in 2-amino-3-cyano-4

Language: Английский

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Acid-Promoted Multicomponent Reaction To Synthesize 4-Phosphorylated 4H-Chromenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8531 - 8536

Published: June 5, 2024

An effective multicomponent reaction for the synthesis of 4-phosphorylated 4H-chromenes via a tandem phosphorylation/alkylation/cyclization/dehydration sequence with water as only byproduct was developed. Extensive mechanistic investigations involving in situ NMR experiments, time control and HRMS experiment allowed us to elucidate order each subreaction arrive at complete understanding underlying mechanism this reaction. Mechanistic data confirm that begins phospha-aldol-elimination, followed by addition ketone enolate, intermolecular alkylation, intramolecular cyclization, dehydration under acidic conditions.

Language: Английский

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ZnO-ZnS Heterostructure as a Potent Photocatalyst in the Preparation of Some Substituted Chromenes and Remarkable Antigastrointestinal Cancer Activity

ACS Omega, Journal Year: 2023, Volume and Issue: 8(46), P. 44276 - 44286

Published: Nov. 10, 2023

The nanosized hybrid material ZnO-ZnS was synthesized using the well-known sol-gel method, as a simple and environmentally friendly procedure. then characterized various techniques including FESEM, TEM, UV-vis, DRS, EDS, XRD, FT-IR. characterization studies revealed generation of nanoparticles with mean size around 25 nm. Moreover, DRS analysis provided band gap 3.05 eV for this nanomaterial. photocatalytic properties heterojunction investigated in synthesis some substituted chromenes under mild reaction conditions. results showed that prepared nanophotocatalyst exhibits significantly higher activity compared to its individual components (ZnO ZnS) provides 73-87% yield 0.01 g after 30 min. In addition, demonstrated high reusability desired condensation reaction. enhanced can be attributed slower recombination electron-hole pairs semiconductor material. reactive species OH•, •O2-, h+ are believed play important roles system. Furthermore, cellular toxicity evaluated on HCT-116 human gastrointestinal cancer cell line by MTT assay. proved distinct reduction viability, proofing cytotoxicity cells. This study highlights potential against cancer.

Language: Английский

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A Brief Review on the Synthesis of 4H‐Chromene‐Embedded Heterocycles

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(27)

Published: July 12, 2024

Abstract Chromenes are an essential class of oxygen‐containing heterocyclic compounds with intriguing biological activity. It is important moiety for the discovery new drug candidates. naturally abundant as alkaloids, tocopherols, flavones, and anthocyanins. The incorporation 4 H ‐chromene, along various bioactive heterocycles such indole, pyrazole, kojic acid, pyran‐2‐one, quinoline, pyridine, pyrimidine, coumarin, sesamol, furan, uracil, benzoimidazole, benzotriazole, thiazole, isoxazole barbituric acid moieties, into a molecular scaffold has potential to combine properties both components. synergistic effect combining different moieties within ‐chromene nucleus results in formation valuable significant importance. This review summarizes synthetic techniques used preparing ‐chromene‐embedded heterocycles. common mechanisms key reactions significance method discussed.

Language: Английский

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Recent Advances on Synthesis of 2H‐Chromenes, and Chromenes Fused Hetrocyclic Compounds

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 12, 2024

Abstract Chromenes and 2H ‐Chromenes are vital components of natural products, pharmaceuticals, agrochemicals that have captured the attention researchers worldwide. These heterocyclic compounds represent an essential class structural scaffolds, quest for their synthesis in a mild straightforward way has gained significant momentum. oxygen‐containing heterocycles been widely studied due to potential medicinal properties. In last two decades, made remarkable progress towards chromene based using O‐propargylated benzaldehydes as substrate. substrates highly versatile contain functional groups make them ideal wide range reactions. This review article provides in‐depth analysis latest advances alkynes’ functionalization, emphasizing substrate scope, limitations, regioselectivity control, applications these The also covers critical methods strategies, including multicomponent reactions, used general numerous types derivatives.

Language: Английский

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Asymmetric catalytic Friedel–Crafts alkylation with arenes and heteroarenes: construction of 3,3-disubstituted oxindoles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5274 - 5283

Published: Jan. 1, 2023

The asymmetric Friedel–Crafts alkylation of 3-bromo-3-substituted oxindoles with arenes and heteroarenes was achieved to synthesize enantioenriched C3-arylated oxindoles.

Language: Английский

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Ultrasound Assisted Domino Strategy for the Synthesis of 2‐Aryl‐4‐(indol‐3‐yl)‐4H‐chromenes under Mild Conditions

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(2)

Published: Jan. 1, 2025

Abstract An efficient and practical approach has been developed for the rapid synthesis of indolyl‐chromene derivatives. Ultrasound assisted three component reaction salicylaldehyde, acetophenone indole leads to indolyl 4 H ‐chromene products in good yields. Pyrrolidine base ethanol medium are employed achieve desired compounds within short time at room temperature. We have also shown catalytic activity usefulness present method by describing TOF TON measurement. Beside includes a metal‐free process, greener solvent, broad range substrate scope, mild conditions.

Language: Английский

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Formation of 2H- and 4H-chromene Rings in Intramolecular Rauhut–Currier Reaction, Catalyzed by Lithium Selenolates

ACS Omega, Journal Year: 2025, Volume and Issue: 10(4), P. 3652 - 3664

Published: Jan. 22, 2025

In this paper, we present the first example of using a catalytic amount nucleophilic seleno-organic catalyst in tandem seleno-Michael/Michael reaction, leading to formation 2H/4H-chromenes. Chromenes represent highly significant group oxygen-containing heterocycles commonly found as structural scaffolds diverse range fields such medicinal chemistry, pharmaceutical agents, drug candidates, synthetic and materials chemistry. Various preparation methods have been developed, utilizing different substrates conjunction with metal catalysts, organocatalysts, Brønsted acids, bases, or Lewis acids. The utility lithium selenolates has demonstrated efficient catalysts Rauhut–Currier cyclization chalcone derivatives. This methodology allows for synthesis 2H- 4H-chromenes depending on substituents directly connected carbonyl group. investigation focuses impact various aromatic fragment well conditions selenolates. scope starting was also considered.

Language: Английский

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Regioselective 1,4-Addition of P(O)–H Species to In Situ-Formed 1-Benzopyrylium Ion from C3-Substituted 2H-Chromene Hemiketals to Construct C3-Functionalized C4-Phosphorylated 4H-Chromenes

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(5), P. 1768 - 1783

Published: Jan. 24, 2025

Herein, we report the first example that P(O)-H species including H-phosphonates and H-phosphine oxides could participate in a highly regioselective 1,4-addition to situ generated 1-benzopyrylium ion from C3-substituted 2H-chromene hemiketals, which provides brand-new effective approach for synthesis of C4-phosphorylated 4H-chromenes with diverse C3-functionality (ketone, ester, sulfonyl, aryl, alkyl groups). In total, reaction features use inexpensive Zn(ClO4)2·6H2O as catalyst, low catalyst loading (only 5 mol %), mild conditions (60 °C, 10 min 24 h), broad substrate scope (46 examples) well good high yields (>90% yield on average). More importantly, mechanistic experiments demonstrated essential role C3-substituent hemiketals stabilizing control.

Language: Английский

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