Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7188 - 7198

Published: May 12, 2023

Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines quinolines. The selective products can be achieved by employing enaminones or enaminones/anilines reaction partners. In addition, compared with using conventional aldehyde synthons, rongalite displays an evident advantage in providing considerably higher product yields under milder conditions. GC-MS analysis process performed to probe possible mechanism.

Language: Английский

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Harnessing molecular hybridization approach to discover novel quinoline EGFR-TK inhibitors for cancer treatment

Future Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 16(11), P. 1087 - 1107

Published: May 9, 2024

Aim: Using molecular hybridization approach, novel 18 quinoline derivatives (6a–11) were designed and synthesized as EGFR-TK inhibitors. Materials & methods: The antiproliferative activity was assessed against breast (MCF-7), leukemia (HL-60) lung (A549) cancer cell lines. Moreover, the most active (6d 8b) further investigated for their potential In addition, cycle analysis apoptosis induction conducted. Results: A considerable cytotoxic attained with IC50 values spanning from 0.06 to 1.12 μM. Besides, 6d 8b displayed potent inhibitory EFGR of 0.18 0.08 μM, respectively. Conclusion: Accordingly, afforded can be used promising lead anticancer candidates future optimization.

Language: Английский

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Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(9)

Published: July 29, 2023

Abstract Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, use transition metal catalysts or additives MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest metal‐free N ‐heterocyclic compounds. This review provides comprehensive concise overview advancements valuable ‐heterocycles over past five years. The is systematically organized, categorizing discussed based on size heterocyclic ring number nitrogen atoms. Only that result formation rings containing at least one atom are included, while derivatization using falls outside scope this review. By highlighting developments field, aims showcase potential significance sustainable strategies accessing elimination metals not only simplifies reaction conditions but also contributes greener more environmentally friendly approaches. serves resource researchers interested design application

Language: Английский

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Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(23), P. 6484 - 6489

Published: Jan. 1, 2022

We herein report an efficient and green aerobic radical cascade reaction of o -vinylphenylisocyanides with thiols to access a broad range 2-thio-substituted quinolines without the need for additional catalysts or oxidants.

Language: Английский

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A Review on Synthesis and Biological Applications of Quinoline Derivative as Fused Aromatic Compounds

Polycyclic aromatic compounds, Journal Year: 2023, Volume and Issue: unknown, P. 1 - 30

Published: Oct. 27, 2023

Quinoline is a N-containing heterocyclic organic compounds with significant biological importance in pharmaceuticals field as well natural products. They exhibit excellent pharmacological activities. To synthesize quinoline and their derivatives several synthetic methods have reported, such conventional method, ultrasonic microwave (MW) irradiation or without catalytic reaction, which various activities, antibacterial, antifungal, anticancer, anti-HIV, antimalarial, antitumor, anti-inflammatory activity. The objective of this review to compile were used for the formation importance, anti-microbial, antileishmanial, during 2010–2023, will help researchers how are working area.

Language: Английский

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Copper-Catalyzed [4+1+1] Annulation of Ammonium Salts and Anthranils: Synthesis of 2,3-Diaroylquinolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7446 - 7454

Published: May 15, 2024

A copper(I)-catalyzed protocol is developed for the synthesis of various 2,3-diaroylquinolines starting from achiral ammonium salts and anthranils through [4+1+1] annulation. Using copper(I) chloride as sole catalyst, this reaction featured with easily available materials, broad substrate scope, good yields simple conditions.

Language: Английский

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Tertiary amines as a C1 synthon: metal-free synthesis of quinolines and 2-substituted quinolinesvia[3+2+1] aerobic cyclization and C–N bond cleavage

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(11), P. 5155 - 5159

Published: Jan. 1, 2023

An I 2 -mediated aerobic cyclization reaction of anilines, alkynes, and tertiary amine has been reported. In this protocol, a novel strategy for the synthesis quinolines using amines as C1 synthon via C–N bond cleavage.

Language: Английский

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Base Metal-Controlled Chemodivergent Cyclization of Propargylamines for the Atom-Economic Synthesis of Nitrogen Heterocycles

Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 9030 - 9035

Published: Nov. 29, 2023

Herein, a base metal-enabled chemodivergent cyclization of propargylamines for the atom-economic construction nitrogen heterocycles has been developed. Due to different modes activation metal propargylamine, copper-catalyzed 6-endo-dig generates functionalized 2-substitued quinoline-4-carboxylates, while iron-promoted cascade amino Claisen rearrangement, aromatization, and aza-Michael addition afford diverse 2-substituted indole-3-carboxylate derivatives. Excellent selectivity, broad functional group tolerance, mild conditions, flexible late-stage functionalization illustrate high efficiency synthetic utility this reaction.

Language: Английский

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Synthesis of Indenoquinolinones and 2-Substituted Quinolines via [4 + 2] Cycloaddition Reaction

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14523 - 14535

Published: Oct. 19, 2022

We have reported a metal-free protocol for the synthesis of indenoquinolinones and 2-substituted quinolines via [4 + 2] cycloaddition reaction using readily available 2-aminobenzaldehydes ketones as starting materials. Different quinoline derivatives can be selectively synthesized by changing type ketones. O2 dimethyl sulfoxide (DMSO) co-oxidants play an important role in indenoquinolinones. This condensation/oxidation strategy involves formation C-N, C-C, C-O bonds, with advantages high yields broad substrate range.

Language: Английский

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Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(3), P. 513 - 520

Published: Dec. 18, 2023

A photoredox radical cascade cyclization reaction for the effective construction of 2,4-disubstituted quinolines at room temperature is described. It shows good substrate suitability and functional group compatibility.

Language: Английский

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