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

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7188 - 7198

Опубликована: Май 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.

Язык: Английский

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Discovery of molecular ferroelectric catalytic annulation for quinolines

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Авг. 7, 2024

Ferroelectrics as emerging and attractive catalysts have shown tremendous potential for applications including wastewater treatment, hydrogen production, nitrogen fixation, organic synthesis, etc. In this study, we demonstrate that molecular ferroelectric crystal TMCM-CdCl3 (TMCM = trimethylchloromethylammonium) with multiaxial ferroelectricity superior piezoelectricity has an effective catalytic activity on the direct construction of pharmacologically important substituted quinoline derivatives via one-pot [3 + 2 1] annulation anilines terminal alkynes by using N,N-dimethylformamide (DMF) carbon source. The recrystallized crystals from DMF remain well piezoelectricity. Upon ultrasonic condition, periodic changes in polarization contribute to release free charges surface domains nano size, which then quickly interacts substrates solution trigger pivotal redox process. Our work advances a route not only providing valuable direction ferroelectrics but also further enriching executable range catalysis. Molecular possess switchable spontaneous polarization. Here, authors show demonstrates evident effects synthesis quinolines.

Язык: Английский

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Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Topics in Current Chemistry, Год журнала: 2022, Номер 380(6)

Опубликована: Окт. 28, 2022

Язык: Английский

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A Pummerer Reaction-Enabled Modular Synthesis of Alkyl Quinoline-3-carboxylates and 3-Arylquinolines from Amino Acids

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3760 - 3771

Опубликована: Фев. 23, 2023

Concise synthesis of functionalized quinolines has received continuous research attention owing to the biological importance and synthetic potential bicyclic N-heterocycles. However, routes 2,4-unsubstituted alkyl quinoline-3-carboxylate scaffold, which is an important motif in drug design, remain surprisingly limited, with modular protocols that proceed from readily available materials being even more so. We herein report acidic I2-DMSO system converts aspartates anilines into quinoline-3-carboxylate. This method can be extended a straightforward 3-arylquinolines by simply replacing phenylalanines. Mechanistic studies revealed DMSO was activated HI via Pummerer reaction provide C1 synthon, while amino acid catabolized C2 synthon through I2-mediated Strecker degradation. A formal [3 + 2 1] annulation these two concurrently generated synthons aniline responsible for selective formation quinoline core. The utility this protocol illustrated efficient human 5-HT4 receptor ligand. Moreover, unprecedented chemoselective 2-deuterated, 3-substituted quinoline, featuring reaction, been established.

Язык: Английский

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Application of N,N-Dimethylethanolamine as a One-Carbon Synthon for the Synthesis of Pyrrolo[1,2-a]quinoxalines, Quinazolin-4-ones, and Benzo[4,5]imidazoquinazolines via [5 + 1] Annulation

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14753 - 14762

Опубликована: Окт. 18, 2022

The synthesis of N-heterocycles composes a significant part synthetic chemistry. In this report, Cu(II)-catalyzed green and efficient pyrrolo[1,2-a]quinoxaline, quinazolin-4-one, benzo[4,5]imidazoquinazoline derivatives was developed, employing N,N-dimethylethanolamine (DMEA) as C1 synthon. Green oxidant O2 is critical in these transformations, facilitating the formation key intermediate─a reactive iminium ion. method conducted under mild conditions compatible with diversity functional groups, providing an appealing alternative to previously developed protocols.

Язык: Английский

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Oxidative Dehydrogenative Coupling of Arylamines with N-allyl and N-vinylamines for the Synthesis of Quinolines and 2-Methylquinoline Derivatives

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134450 - 134450

Опубликована: Янв. 1, 2025

Язык: Английский

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Transition-Metal-Free Multicomponent Polyannulations of Dimethyl Sulfoxide, Amines, and Aldehydes toward Poly(phenylquinoline)s

Chinese Journal of Polymer Science, Год журнала: 2025, Номер unknown

Опубликована: Май 15, 2025

Язык: Английский

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DMSO as a dual carbon synthon in one-pot tandem synthesis of N-alkylated quinazolinones from anthranilamides and acetophenones

New Journal of Chemistry, Год журнала: 2022, Номер 46(34), С. 16289 - 16296

Опубликована: Янв. 1, 2022

DMSO-assisted approach for the synthesis of N -alkylated quinazolinones from readily available 2-aminobenzamide and aryl methyl ketones has been developed. DMSO played a dual role, acting as solvent well carbon synthon, making this process an environmentally benign approach.

Язык: Английский

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DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups

Molecules, Год журнала: 2023, Номер 28(15), С. 5635 - 5635

Опубликована: Июль 25, 2023

Organic thioethers play an important role in the discovery of drugs and natural products. However, green synthesis organic sulfide compounds remains a challenging task. The convenient efficient 5-alkoxy-3-halo-4-methylthio-2(5H)-furanones from DMSO is performed via mediation 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), affording facile route for sulfur-functionalization 3,4-dihalo-2(5H)-furanones under transition metal-free conditions. This new approach has demonstrated functionalization non-aromatic Csp2-X-type halides with unique structures containing C-X, C-O, C=O C=C bonds. Compared traditional methods using metal catalysts ligands, this reaction many advantages, such as lower temperature, shorter time, wide substrate range good functional group tolerance. Notably, plays multiple roles, simultaneously used odorless methylthiolating reagent safe solvent.

Язык: Английский

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Dimethyl Sulfoxide Provides Three Different Units in Synthesis of Chroman-4-ones Containing Sulfur and a Quaternary Carbon Center under HOAc Conditions

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13466 - 13474

Опубликована: Сен. 21, 2023

HOAc-promoted construction of chroman-4-ones with a sulfur atom and an α-carbonyl quaternary carbon center directly from ortho-hydroxyacetophenones DMSO is described. In these unique reactions, activated by HOAc provides three different units (CH2, CH2OH, CH2SMe) in the target molecules. This reaction displays good substrate scope yields series substitutes. The mechanism showed that were formed sequential order.

Язык: Английский

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