Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne DOI Open Access

Sachie Yamamoto,

Naruki Ishida,

Takeshi Yasuda

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(7)

Опубликована: Май 23, 2023

Abstract The Povarov reaction is a representative multicomponent used for synthesizing nitrogen‐containing aromatic compounds from amines, aldehydes, and dienophiles, such as electron‐rich alkenes alkynes. In this study, we investigated triple of 1,3,5‐triaminobenzne with aldehydes phenylacetylene to obtain triazatriphenylene derivatives. Reactions arylaldehydes containing electron‐donating groups proceeded smoothly provide contrast, reactions electron‐withdrawing resulted in low yields. are probably more favorable terms high stability imine intermediates smooth electrophilic cyclization. Single‐crystal X‐ray structure analysis revealed that the aryl derived had small dihedral angles between core. derivative tertiary butyl ( tBu‐TaT ) glass transition temperature, while without H‐TaT lower highest occupied molecular orbital (HOMO) lowest unoccupied (LUMO) level served an efficient hole‐blocking material better electron transport properties than those . This study provides insights into scope limitations based on reaction, substituent dependence crystal structures, physical π‐extended compounds.

Язык: Английский

Recent advances in transition metal-free annulation toward heterocycle diversity based on the C–N bond cleavage of enaminone platform DOI
Xiao Yun Chen, Xiaotong Zhang, Jie‐Ping Wan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(12), С. 2356 - 2369

Опубликована: Янв. 1, 2022

Enaminones and analogous stable enamines are well known as platform building blocks in organic synthesis for the construction of heterocyclic compounds, especially N-heterocycles. To date, enaminones have been successfully employed various 5- or 6- membered heterocycles. Recently, synthetic protocols accomplished by diversity-oriented annulation reactions based on C-N bond cleavage gained notable success. In this review, development transition metal-free product featuring a is reviewed.

Язык: Английский

Процитировано

78

The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

и другие.

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

2‐Hydroxy‐3‐(Pyrrolidin‐1‐yl)‐Indolines: A Platform for Accessing Decorated Deaminokynurenines Enabled by a Double Tautomeric Control DOI
Keisuke Tokushige, Takumi Abe

Asian Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 1, 2025

Abstract In this study we introduce indoline hemiaminals as phenacyl bromide surrogates for the synthesis of deaminokynurenine derivatives through cyclic‐linear tautomeric intermediates. The reaction proceeds a tandem process involving ring opening hemiaminals, generating transient acyclic aldehydes which are then trapped with in situ generated enolate species. Our protocol overcomes traditional dilemma production polar‐mismatch 1,4‐dicarbonyl compounds by utilizing highly electrophilic linear aldehyde and late‐stage transposition carbonyl moiety. synthetic utility our transformation was demonstrated follow‐up transformations, including first total quinoline‐2,4‐dione alkaloid.

Язык: Английский

Процитировано

0

Dinuclear oxidovanadium complexes with dihydrazone ligands derived from diethyl 2,6-dimethylpyridine-3,5-dicarboxylate obtained from Hantzsch reaction; crystal structure and catalytic activity DOI
Fatemeh Soltani, Rahman Bikas, Neda Heydari

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(13), С. 6102 - 6113

Опубликована: Янв. 1, 2023

Hantzsch pyridine ester has been used as a precursor for the synthesis of dihydrazone ligands. Two dinuclear V( v ) complexes obtained by these ligands show high catalytic activity in oxidation sulfides.

Язык: Английский

Процитировано

7

Palladium-Catalyzed E-Selective Oxidative Amination of Aromatic Amine with 3-Butenoic Acid DOI
Qianqian Liu, Zheng Zhou, Zhibin Huang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 15350 - 15357

Опубликована: Окт. 23, 2023

A palladium-catalyzed oxidative amination of inactive olefins with an aromatic amine was developed using a copper acetate oxidant to yield corresponding secondary and tertiary enamines in moderate good yields. This new procedure outlines efficient approach for the construction enamine skeletons.

Язык: Английский

Процитировано

5

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions DOI
Brenno A. D. Neto, Marcos N. Eberlin, James Sherwood

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(30)

Опубликована: Май 11, 2022

Abstract In the current Perspective article, we critically review and discuss importance of solvent effects on multicomponent reactions, likely most neglected aspect in this research field. Although solvent‐free reactions may be desirable sometimes, still require a to properly promote them. This requirement makes knowledge all drawbacks advantages each central issue when trying optimize reactions. Yet, only few studies with actual evidence these key have been published. For quantitative solvents, are even scarcer. Perspective, argue that greater efforts should directed such fundamental studies.

Язык: Английский

Процитировано

7

Development of Mefloquine-Based Bifunctional Secondary Amine Organocatalysts for Enantioselective Michael and Friedel–Crafts Reactions DOI
Dawid J. Kucharski, Radosław Suchanek, Rafał Kowalczyk

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 111 - 123

Опубликована: Дек. 9, 2023

The chiral framework based on 11-aminomefloquine has been utilized for the first time to construct bifunctional organocatalysts. These catalysts demonstrate high enantioselectivity in both Michael additions and Friedel-Crafts reactions across a variety of substrates, achieving up >99% ee. distinctive feature is incorporation secondary amine group, offering unique tight hydrogen-bonding capabilities protonated state, as supported by DFT computation. diversity these organocatalysts suggests their broad applicability multiple reaction classes.

Язык: Английский

Процитировано

3

Anticorrosive Effect of Halogenated Aniline Enaminoesters on Carbon Steel in HCl DOI Creative Commons
Mariana Falcão Lopes Princisval Carlos, Geicy K. P. Barboza, Aurea Echevarrı́a

и другие.

International Journal of Corrosion, Год журнала: 2022, Номер 2022, С. 1 - 15

Опубликована: Май 27, 2022

Four enaminoesters derived from halogenated aniline, with potential anticorrosion activity, were synthesized and tested against carbon steel AISI 1020 in acid medium using 1.0 mol L-1 HCl. The synthesis was demonstrated through the reaction of ethyl acetoacetate four different amines, presence glacial acetic molecular sieve, ethanol as solvent for 24 h. evaluation anticorrosive activity performed gravimetric technique electrochemical methods, such impedance spectroscopy (EIS), linear polarization resistance (LPR), potentiodynamic (PP). Results indicated that F-EN (Ethyl (2Z)-3-[(4-fluoro-phenyl)-amino]-but-2-enoate) inhibitor had higher corrosion inhibition efficiency, 98% by mass loss, 85% techniques. Adsorption obeyed Langmuir isotherm, thus suggesting inhibitors form a monolayer film metal surface. These results also contributed to calculations physicochemical parameters Ea , Hads Sads which confirmed when compared absence inhibitors.

Язык: Английский

Процитировано

5

Synthesis of novel pyrrole derivatives from the multicomponent reaction using the new N‐sulfonic acid modified poly (styrene‐diethylenetriamine) as a solid acid catalyst DOI
Taraneh Abbaspour, Ghasem Firouzzadeh Pasha, Mahmood Tajbakhsh

и другие.

Applied Organometallic Chemistry, Год журнала: 2022, Номер 37(1)

Опубликована: Окт. 19, 2022

An efficient acid‐catalyzed synthesis of 1,5‐diaryl‐3‐(arylamino)‐1 H ‐pyrrol‐2(5 )‐ones is reported using novel N ‐sulfonic acid modified poly (styrene‐diethylenetriamine) through three‐component reaction between aldehyde, amine, and ethyl pyruvate in high yields short times. This heterogeneous solid catalyst produced by reacting amine‐modified chloromethyl polystyrene with neat chlorosulfonic acid. The structure the synthesized was examined Fourier transform‐infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), dynamic light scattering (DLS), thermogravimetric analysis (TGA), differential thermal (DTA), scanning electron micrograph (SEM), Brunauer–Emmett–Teller (BET), energy dispersive (EDS), elemental analyses. has many advantages, including an easy work‐up procedure, a product yield, capability to be easily regenerated reused for at least five cycles without losing its activity.

Язык: Английский

Процитировано

5

Introducing a new magnetic nanocomposite based on the chitosan modified by sulfonic acid-containing moieties for synthesis of 1,4-dihydropyridines and polyhydroquinolines DOI
Maryam Shahsavari, Mohammad Piltan

Research on Chemical Intermediates, Год журнала: 2023, Номер 49(11), С. 4845 - 4863

Опубликована: Сен. 1, 2023

Язык: Английский

Процитировано

2