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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Base-Controlled Divergent Synthesis of 5-Cyanobenzoxepines and Benzofuro[2,3-b]pyridines from 2-Bromophenylacetonitriles and Ynones

Organic Letters, Journal Year: 2019, Volume and Issue: 21(14), P. 5457 - 5461

Published: July 8, 2019

An effective base-controlled divergent annulation reaction of 2-bromophenylacetonitriles and ynones has been developed. Various functionalized 5-cyanobenzoxepines benzofuro[2,3-b]pyridines were obtained with a broad substrate scope high regioselectivity in moderate to excellent yield. Of importance, an unexpected O-rearrangement access was observed using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base, possible mechanism supported by 18O-labeled experiments. In addition, gram-scale synthesis further transformation product studied.

Language: Английский

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Synthesis of 1,4-Thiazepines

The Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 83(15), P. 8376 - 8389

Published: June 24, 2018

An efficient, general, and unprecedented methodology for the synthesis of 2-methylene-2,3-dihydro-1,4-thiazepines from N-propargylic β-enaminones is described. Initially, were thionated with Lawesson's reagent in good to high yields, then resulting β-enaminothiones subjected electrophilic cyclization. When treated zinc chloride refluxing chloroform, underwent cyclization yield yields. A general trend was observed all β-enaminothiones, proceeded efficiency large functional group tolerance. This process also applicable internal alkyne-tethered β-enaminothiones. operationally simple facile method may represent a very rapid entry library functionalized 1,4-thiazepines area pharmaceuticals.

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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One-pot synthesis of iodine-substituted 1,4-oxazepines

Tetrahedron Letters, Journal Year: 2018, Volume and Issue: 59(9), P. 823 - 827

Published: Jan. 31, 2018

Language: Английский

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Zinc Chloride Mediated Synthesis of 3H‐Oxazol‐2‐one and Pyrrolo‐oxazin‐1‐one from Ynamide

European Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 2019(31-32), P. 5175 - 5179

Published: April 25, 2019

A simple zinc chloride mediated cyclization of ynamidyl N ‐carbamates or 2‐ynamidyl‐(hetero)arylcarboxylates is achieved under mild reaction conditions, leading to the synthesis useful heterocyclic scaffolds, 3 H ‐oxazol‐2‐ones and pyrrolo‐oxazin‐1‐ones, with good yields.

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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Divergent Synthesis of Unsymmetrical Bis-heteroaryl Ketones via Base-Promoted Cascade Reactions of 1,2-Alkynedione-Derived N-Propargylic β-Enaminones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11665 - 11670

Published: Aug. 6, 2024

Herein we disclose a transition-metal-free, one-pot two-step strategy for the synthesis of unsymmetrical bis-heteroaryl ketones.

Language: Английский

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N‐Propargylic β‐enaminones in breast cancer cells: Cytotoxicity, apoptosis, and cell cycle analyses

Journal of Biochemical and Molecular Toxicology, Journal Year: 2023, Volume and Issue: 37(4)

Published: Jan. 16, 2023

Breast cancer is one of the most common cancers worldwide and discovery new cytotoxic agents needed. Enaminones are regarded to be a significant structural motif that found in variety pharmacologically active compounds however number studies investigating anticancer activities N-propargylic β-enaminones (NPEs) limited. Herein we investigated potential apoptotic effects 23 different NPEs (1-23) on human breast cells. Cytotoxicity was evaluated via MTT assay. Apoptotic cell death cycle distributions were by flow cytometry. CM-H2DCFDA dye used evaluate cellular ROS levels. Expression levels Bcl-2, Bax, p21, Cyclin D1 measured quantitative real-time PCR. ADME properties calculated using ADMET 2.0 tool. 4, 9, 16, 21 showed selective activity against cells with SI values >2. induced apoptosis caused changes Bcl-2 Bax mRNA The arrested at G0/G1 phase p21 upregulated both significantly increased NPEs, suggesting mediated ROS. analysis revealed favorable lines, meaning good lipophilicity values, low unfractionated high bioavailability. Therefore, these should further validated vivo for their appropriate function health safety profile, comprehensive drug interaction study performed.

Language: Английский

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Synthesis of 3‐Keto Pyridines from the Conjugated Allenone – Alkynylamine Oxidative Cyclization Catalyzed by Supported Au Nanoparticles

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(4), P. 964 - 968

Published: Jan. 3, 2020

Abstract Recyclable supported Au nanoparticles on TiO 2 catalyze the cyclization of N ‐propargyl or ‐homopropargyl β‐enaminones followed by dehydrogenation (aromatization) leading to substituted 3‐keto pyridines 4‐picolines in very good yields. This pathway is contrast their known presence Au(I) Au(III) catalysts which provides 1,4‐oxazepines, instead. The enaminones are formed situ upon mixing a conjugated allenone allenyl ester with alkynylamine, thus pyridine‐forming transformation typically one pot process. magnified image

Language: Английский

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