Facile synthesis of the unknown 6,7-dihydrofuro[3,4-c]pyridines and 3,4-diaryloylpyridines from N-propargyl β-enaminones

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A simple methodology for the synthesis of bicyclic 6,7-dihydrofuro[3,4- c ]pyridines is reported. The skeletal diversity synthesized heterobicyclic frame may present new nitrogen- and oxygen-based hybrid systems medicinal chemistry.

Language: Английский

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Indole‐based novel organic anode catalyst for glucose electrooxidation

International Journal of Energy Research, Journal Year: 2021, Volume and Issue: 46(2), P. 1659 - 1671

Published: Sept. 20, 2021

The development of organic-based metal-free catalysts is vital for the commercialization fuel cells. At present, novel indole derivatives (2-((5-(5-[1-Methyl-2-phenyl-1H-indol-3-yl] thiophen-2-yl)furan-2-yl) methylene) malononitrile ITFM and 2-((5′-(1-Methyl-2-phenyl-1H-indol-3-yl)-(2,2′-bithiophen)-5-yl)methylene) ITTM were designed, synthesized, their electrochemical properties investigated. First, one-pot two-step cyclization reactions applied synthesis intermediate 1-methyl-2-phenyl-3-(thiophen-2-yl)-1H-indole (5). Then, halogenation reaction Suzuki-Miyaura coupling used formation 5-(5-[1-methyl-2-phenyl-1H-indol-3-yl] thiophen-2-yl) furan-2-carbaldehyde (8) 5′-(1-methyl-2-phenyl-1H-indol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde (12). Finally, isolated in 76% 60% yields via condensation reactions. glucose electrooxidation performance these examined by using Cyclic Voltammetry (CV), Chronoamperometry (CA), Electrochemical Impedance Spectroscopy (EIS) 0.5 M alkaline solution. exhibited best activity because specific was found as 0.46 mA/cm2, gave 0.52 mA/cm2. CA results revealed that stability greater than catalysts. EIS also agreement with CV charge transfer resistance (Rct) displaying improved charge-transfer kinetics. As a result, an derivative-based catalyst new generation environmentally friendly alternative direct

Language: Английский

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One-Pot Synthesis of 2-Acetyl-1H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(9), P. 6289 - 6304

Published: April 19, 2021

A one-pot two-step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic β-enaminones was described. When treated with zinc chloride in refluxing chloroform, produced situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further methanol chloride, afforded 2-acetyl-1H-pyrroles. The process found to be general a wide variety and yielded diverse range good high yields large substrate scope functional group tolerance. This operationally easy method may provide rapid access functionalized pharmacological interest.

Language: Английский

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Synthesis of 3-[(4-Nitrophenyl)thio]-Substituted 4-Methylene-1-pyrrolines from N-Propargylic β-Enaminones

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(7), P. 4937 - 4950

Published: March 10, 2020

A facile and efficient method for the synthesis of 3-[(4-nitrophenyl)thio]-substituted 4-methylene-1-pyrrolines is described. When treated with 4-nitrobenzenesulfenyl chloride in refluxing acetonitrile, N-propargylic β-enaminones produced α-sulfenylated β-enaminones, which, presence sodium hydride or cesium carbonate, underwent nucleophilic cyclization to afford 4-methylene-3-[(4-nitrophenyl)thio]-1-pyrrolines good high yields. It was shown first time that on β-enaminone systems, α-sulfenylation dominates over formation thiirenium ion. This one-pot two-step process found be general a variety demonstrated tolerance diversity aromatic heteroaromatic groups electron-withdrawing electron-donating substituents. also applicable internal alkyne-tethered β-enaminones. The enrichment 1-pyrroline core an aryl sulfide moiety might exhibit potential molecules pharmacological interest.

Language: Английский

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One-Pot Sequential Hydroamination Protocol for N-Heterocycle Synthesis: One Method To Access Five Different Classes of Tri-Substituted Pyridines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(3), P. 1378 - 1384

Published: Jan. 12, 2023

Tri-substituted pyridines are important scaffolds that can be found in a plethora of commercially available drugs. A one-pot general method for the selective synthesis less explored/challenging patterns tri-substituted is described. Hydroamination alkynes with N-triphenylsilylamine generates N-silylenamines. These situ generated N-silylenamines, upon reaction α,β-unsaturated carbonyl compounds and subsequent oxidation, furnish 25 examples selectively substituted 2,4,5-, 2,3,4-, 3,4,5-, 2,3,5-, 2,3,6-trisubstituted up to 78% yield. The features high functional group compatibility providing an expeditious approach assembly pyridine derivatives. robustness practicality have been demonstrated gram-scale reaction.

Language: Английский

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Design, Synthesis, and In vitro Evaluation of Thieno[a]dibenzothiophene Derivatives

ChemistrySelect, Journal Year: 2020, Volume and Issue: 5(12), P. 3700 - 3709

Published: March 26, 2020

Abstract A variety of highly substituted thieno[2,3‐a]dibenzothiophenes and thieno[3,2‐ a ]dibenzothiophenes are readily prepared via cascade electrophilic cyclization reaction. The reaction was tolerated compounds. In the present study, antimicrobial antifungal activities were investigated for all synthesized molecules against A. niger ATCC 16404, C. albicans 10231, S. aureus 25923 B. subtilis 6633, respectively.

Language: Английский

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A facile synthesis of 6-chloro-2-methylene-2,3-dihydro-1,4-oxazepines from N-propargylic β-enaminones

Tetrahedron, Journal Year: 2020, Volume and Issue: 76(48), P. 131650 - 131650

Published: Oct. 16, 2020

Language: Английский

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Base‐Promoted Synthesis of 3‐Alkenyl‐2‐pyridones from N‐Propargyl‐β‐enaminones and Aryl Aldehydes

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 39(10), P. 2781 - 2788

Published: June 27, 2021

Main observation and conclusion In this article, we report a base‐promoted sequential cyclization/aldol‐type condensation/isomerization cascade reaction of N ‐propargyl‐β‐enaminones with aryl aldehydes. The key step in protocol is the generation 1,4‐oxazepine anions from under basic conditions, which are captured by method allows formation one pyridone core C—C double bond “one pot”, preparation variety densely decorated derivatives moderate to good yields broad functional group tolerance.

Language: Английский

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A New Strategy for the Synthesis of 4‐Propargyl‐Substituted 1H‐Pyrroles from N‐(5‐phenyl‐2,4‐pentadiynyl) β‐Enaminones

ChemistrySelect, Journal Year: 2019, Volume and Issue: 4(37), P. 11043 - 11047

Published: Oct. 1, 2019

Abstract A new method for the synthesis of 4‐propargyl‐substituted 1 H ‐pyrroles is described. When treated with sodium hydride in refluxing dichloromethane, N ‐(5‐phenyl‐2,4‐pentadiynyl) β‐enaminones, synthesized by coupling ‐propargylic β‐enaminones phenylacetylene, afforded pyrrole derivatives. This conversion was general a variety and displayed broad functional group tolerance. During reaction, not only cyclization linear precursors to ring takes place, but also propargyl introduced core one‐pot. The enrichment compounds unit might exhibit potential heterocyclic molecules pharmacological interest.

Language: Английский

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Chemoselective synthesis of β-enaminones from ynones and aminoalkyl-, phenol- and thioanilines under metal-free conditions

Chemical Papers, Journal Year: 2021, Volume and Issue: 75(7), P. 3625 - 3634

Published: March 27, 2021

Language: Английский

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