Article
Chemistry, Physical
Allison M. M. Hawks, Drake Altman, Ryan Faddis, Ethan M. M. Wagner, Kenneth-John J. Bell, Ariane Charland-Martin, Graham S. S. Collier
Summary: This study synthesized DHPP chromophores with various electron-donating or electron-withdrawing capabilities and investigated their optoelectronic properties. The results showed distinct differences in UV-vis absorbance spectra and oxidation onsets, as well as different absorbance profiles of the radical cations corresponding to different colors. Two chromophores also exhibited high-contrast electrochromism, making them potentially useful in electronic devices.
JOURNAL OF PHYSICAL CHEMISTRY B
(2023)
Article
Chemistry, Organic
Shuo Wang, Shi-Jie Ma, Ji-Cong Lou, Wen-Wu Sun, Bin Wu
Summary: The copper-catalyzed cycloaddition reaction of N-hydroxysuccinimide ester and isocyanatoacetate was reported, resulting in a series of 4,5-disubstituted oxazole compounds, including those derived from natural fatty acids, drugs, amino acids, and peptides, with moderate to high yields. The derivatization reaction and mechanism were also explored.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Dirgha Raj Joshi, Ikyon Kim
Summary: In this study, a modular approach was used to synthesize a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization. DDQ was utilized for the first time to selectively synthesize the pyrrole units from cyclopropyl pyridines. The regioselective oxidation of the benzylic position by DDQ enabled the access to one regioisomer out of two possible ones. Additionally, homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ was discovered for the first time.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Wei-Cheng Yuan, Xin-Meng Chen, Jian-Qiang Zhao, Yan-Ping Zhang, Zhen-Hua Wang, Yong You
Summary: In this study, a novel Ag-catalyzed asymmetric reaction was developed to achieve the dearomatization of nitroindoles, leading to the synthesis of a variety of optically active tetrahydropyrrolo[3,4-b]indole derivatives with high yields and enantioselectivity. The synthetic potential of this protocol was demonstrated through gram-scale reactions and versatile transformations of the product.
Article
Polymer Science
Sebastian Fortsch, Elena Mena-Osteritz, Peter Baeuerle
Summary: Novel electron-rich building blocks Me-DTP 2-7 were converted to conducting polymers and functional dyes for organic electronic applications, with their structural and optoelectronic properties investigated through quantum chemical calculations to establish valuable structure-property relationships.
Article
Chemistry, Organic
Issa Yavari, Meysam Ghorbanzadeh, Somayeh Akbarzadeh
Summary: A new strategy for the construction of functionalized 2-amino-3-cyano pyrroles has been developed, which involves a copper-catalyzed azide-alkyne cycloaddtion reaction followed by generation of N-sulfonoketenimine intermediates. The reaction proceeded smoothly in THF at ambient temperature to afford the target compounds in good yields and regioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Electrochemistry
Sema Topal, Sebahat Topal, Pelin Ulukan, Belkis Ustamehmetoglu, Turan Ozturk, Esma Sezer
Summary: Two novel polymers, P[FPhTT] and P[FPhTT], were synthesized by electropolymerization and characterized for their electrochemical properties and surface characteristics, showing potential applications in energy storage and electrochromic devices.
ELECTROCHIMICA ACTA
(2021)
Article
Chemistry, Multidisciplinary
Priscila Pazini Abatti, Nicolas Oliveira Decarli, Szymon Gogoc, Przemyslaw Data, Ivan H. Bechtold, Eduard Westphal, Hugo Gallardo
Summary: Three tetraaryl-1,4-dihydropyrrolo[3,2-b]pyrrole derivatives with different numbers of long alkoxy chains were synthesized and applied in OLEDs. These compounds showed good emission properties and exhibited different emission features in solution and solid state. Additionally, the compounds formed aggregates with redshifted emission.
Article
Polymer Science
Tam Huu Nguyen, Le-Thu T. Nguyen, Mai Ha Hoang, Thiet-Quoc Nguyen, Son Thanh Cu, Ryota Simada, Yoshihiro Ohta, Tsutomu Yokozawa, Ha Tran Nguyen
Summary: The nonstoichiometric Suzuki-Miyaura polycondensation using t-Bu3PPd G2 precatalyst is an efficient method for synthesis of high molecular weight π-conjugated copolymers based on N-acyl DTPs. The Pd catalyst effectively walks on N-acyl DTPs, allowing for the selective preparation of disubstituted products. By utilizing excess dibromo-N-acyl DTPs with arylenediboronic acid esters, a series of novel N-acyl DTP-based copolymers with high Mn (up to 195 kDa) were successfully prepared.
EUROPEAN POLYMER JOURNAL
(2023)
Article
Chemistry, Organic
Alla I. Vaskevych, Nataliia O. Savinchuk, Ruslan I. Vaskevych, Eduard B. Rusanov, Oleksandr O. Grygorenko, Mykhailo V. Vovk
Summary: This method describes a regioselective approach to synthesize 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones, which are structurally similar to naturally occurring vasicinone alkaloids. The products obtained have a high natural product likeness (NPL) score, making them potentially useful for designing natural product-like compound libraries.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Hyokwon Kim, Min Jeong Kim, Kyukwan Zong
Summary: A series of novel diselenopheno[3,2-b:2',3'-d]thiophenes were designed and synthesized, and their optical properties and electrochemical behaviors were investigated in this study.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Denis N. Tomilin, Sophia A. Stepanova, Lyubov N. Sobenina, Igor A. Ushakov, Boris A. Trofimov
Summary: Acylethynylpyrroles, obtained from acylbromoacetylenes and pyrroles, smoothly undergo [3+2]-cyclization with ketones and aldehydes (room temperature) to give acylmethylidenepyrrolo[1,2-c]oxazoles in up to 82% yield, meeting the principles of the PASE paradigm.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
Xing-Hai Fei, Yong-Long Zhao, Fen-Fen Yang, Xiang Guan, Zong-Qin Li, Da-Peng Wang, Meng Zhou, Yuan-Yong Yang, Bin He
Summary: A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed, leading to the synthesis of a series of oxepino[3,2-b]indoles in moderate to excellent yields. These synthetic oxepino[3,2-b]indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. Additionally, the synthetic compounds exhibit certain antiproliferative activity against K562 and MCF-7 cells, with IC50 values up to 5.40 +/- 0.88 μM and 18.41 +/- 0.50 μM, respectively.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Materials Science, Composites
Venkatesan Raja, Zhao Hu, Guangming Chen
Summary: TE composites, especially PBTTT composites, show great potential for converting heat to electricity; PBTTT has advantages over inorganic materials in terms of low heat conductivity and high adjustability; The research on PBTTT TE composites with carbon nanotubes or graphene as constituents is advancing rapidly.
COMPOSITES COMMUNICATIONS
(2021)
Article
Chemistry, Medicinal
Shiqin Cong, Yichun Shi, Guangjun Yu, Feng Zhong, Jingjing Li, Jing Liu, Chanyuan Ye, Zhenghuai Tan, Yong Deng
Summary: Based on previous research, novel 5-(2-hydroxyphenyl)-2-phthalide-3(3H)-pyrazolones derivatives were discovered as potential multifunctional therapeutic agents for Alzheimer's disease. These derivatives showed strong activity against MAO-B, A/31-42 aggregation, oxidative stress, and metal ion dyshomeostasis. Among them, 10x was identified as the most effective agent with excellent MAO-B inhibitory activity, antioxidant activity, and anti-A/3 aggregation activity, as well as significant metal-ion chelating ability, anti-neuroinflammation, and neuroprotective activity. Moreover, in vivo behavioral assessment demonstrated that 10x significantly improved memory and cognitive impairment in a mouse model of AD. Overall, these findings suggest that 10x has the potential to be a balanced multifunctional anti-AD agent and should be further investigated.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Dmitrii A. Shabalin, Evgeniya E. Ivanova, Igor A. Ushakov, Elena Yu Schmidt, Boris A. Trofimov
Summary: Convenient protocols have been developed for the synthesis of three highly functionalized azaheterocyclic scaffolds using readily available hydroxypyrrolines and hydrazides. The transformation of a common initial intermediate, a Bronsted acid-activated hydroxypyrroline, depends on reaction conditions and hydrazide structure.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ludmila A. Oparina, Anastasiya G. Mal'kina, Nikita A. Kolyvanov, Igor A. Ushakov, Ivan V. Saliy, Konstantin A. Apartsin, Boris A. Trofimov
Summary: The ring-opening/functionalization of 1-pyrrolines by cyanoacetylenes or acetylenic ketones in suitable temperature and solvent conditions affords delta-keto aminoacrylonitriles and.-keto aminoenones with high yields. The synthesis involves C(2)-N bond cleavage in the intermediate hemiaminal resulting from the intermediate 1,3(4)-dipolar 1-pyrroline/acetylene complexes and water.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Dmitrii A. Shabalin, Maxim K. Kazak, Igor' A. Ushakov, Alexander V. Vashchenko, Elena Yu. Schmidt
Summary: A convenient synthesis of pyrrolo[2,1-a]isoquino-linium salts from 1-pyrrolines and alkynes through rhodium-catalyzed C-H functionalization/N-annulation tandem reaction is described. The protocol shows good substrate tolerance, mild reaction conditions, and high yields of target products. Exploration of the alkyne scope unexpectedly revealed a novel labile functional group-promoted rhodium-catalyzed C-H functionalization/C-annulation/elimination cascade reaction of 1-pyrrolines with electron-deficient alkynes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Marina A. Borisova, Dmitry S. Ryabukhin, Alexander Yu Ivanov, Irina A. Boyarskaya, Dmitrii A. Shabalin, Lev E. Zelenkov, Elena Yu Schmidt, Boris A. Trofimov, Aleksander V. Vasilyev
Summary: 5-Hydroxy-1-pyrrolines react with arenes in TfOH or H2SO4 to afford 5-aryl-1-pyrrolines, and undergo dehydration in TfOH or H2SO4 to form N-protonated forms of 3H-pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ludmila A. Oparina, Kseniya V. Belyaeva, Nikita A. Kolyvanov, Igor A. Ushakov, Maxim D. Gotsko, Lyubov' N. Sobenina, Alexander V. Vashchenko, Boris A. Trofimov
Summary: Acylethynylpyrroles can undergo catalyst-free annulation with 1-pyrrolines at room temperature, giving acylmethylenetetrahydrodipyrrolo[1,2-a:1 ' ,2 ' -c]imidazoles. The reaction conditions are simple, with high yields and good E-stereoselectivity of the olefin moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Marina Yu. Dvorko, Dmitrii A. Shabalin, Igor A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov
Summary: The cascade dimerization of alkynones with sterically hindered secondary alkyl groups at the carbonyl function unexpectedly produced highly functionalized furans. This reaction efficiently takes place at room temperature in the presence of a potassium tert-butoxide/dimethylsulfoxide superbase catalytic system. Alkynones with an additional C-H active site at the carbon-carbon triple bond followed a different dimerization pathway to form 3-alkenylpyran-4-ones. The discovery of these reactions expands the traditional understanding of alkynone reactivity in strong basic conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Evgeniya E. E. Ivanova, Dmitrii A. A. Shabalin, Igor' A. Ushakov, Alexander V. V. Vashchenko, Elena Yu. Schmidt, Boris A. A. Trofimov
Summary: Tetrahydropyrrolo[1,2-d]oxadiazoles were synthesized in good-to-excellent yields through the cycloaddition of nitrile oxides to readily accessible functionalized Delta(1)-pyrrolines in a two-phase system with sodium hypochloride as an oxidant. The reaction produced diastereoselective 1,2,4-oxadiazolines fused with a five-membered ring, which have pharmaceutical potential. The reaction demonstrated a broad substrate tolerance, including those with oxidant-sensitive functional groups and competitive reaction sites.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Svetlana N. Arbuzova, Svetlana I. Verkhoturova, Sergey V. Zinchenko, Nikita A. Kolyvanov, Nataliya A. Chernysheva, Gaukhar K. Bishimbaeva, Boris A. Trofimov
Summary: In this study, secondary phosphine chalcogenides reacted mildly with aldimines (without catalysts and solvents, at temperatures of 20-65 degrees Celsius for 0.25-65.5 hours) to yield previously unknown alpha-aminophosphine oxides, sulfides, and selenides in good to excellent yields.
Article
Chemistry, Organic
L. A. Oparina, L. A. Grishchenko, N. A. Kolyvanov, I. A. Ushakov, B. A. Trofimov
Summary: Schiff bases reacted with cyanopropargyl alcohols under catalyst-free and solvent-free conditions (80 degrees C, 10-12 h) to give functionalized 1,3-oxazolidines in up to 82% yield. The reaction involves a sequence of transformations, which includes the formation of a 1,3-dipolar intermediate via addition of the neutral N-nucleophile to the activated triple bond, proton transfer from the hydroxy group to the carbanionic center of that intermediate, and intramolecular attack of the oxygen-centered anion on the former C=N carbon atom of Schiff base with closure of 1,3-oxazolidine ring.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dmitrii A. Shabalin, Lev E. Zelenkov
Summary: An expedient synthesis of previously unknown pyrrolo[2,1-a]isoquinolinium salts has been developed by utilizing non-aromatic aryl-substituted 2H- and 3H-pyrroles and internal alkynes. This reaction represents a rare example of N-nucleophilic reaction of 2H- and 3H-pyrroles and relies on the ortho-C-H bond activation of non-aromatic arylpyrroles in the presence of rhodium catalyst followed by alkyne annulation reaction. Diverse substituted salts were obtained in high yields under mild reaction conditions. Moreover, the photophysical properties of selected pyrrolo[2,1-a]isoquinolinium salts have been evaluated, demonstrating their potential applications as fluorescent materials for light-emitting devices and bioimaging.
Article
Chemistry, Organic
Anton V. V. Kuzmin, Dmitrii A. A. Shabalin
Summary: This study focuses on the density functional theory (DFT) investigation of substrate-controlled dimerizations of aliphatic alkynones using base catalysts. Theoretical analysis was conducted to understand the selectivity of cascade reactions and the thermodynamic and kinetic characteristics of deprotonation reactions. The computational results provide valuable insights for predicting the outcomes of related base-catalyzed reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Ludmila A. Oparina, Nikita A. Kolyvanov, Igor A. Ushakov, Lina P. Nikitina, Olga V. Petrova, Lyubov N. Sobenina, Konstantin B. Petrushenko, Boris A. Trofimov
Summary: This study discovered a novel synthetic approach to connect delta(1)- pyrrolines with available pyrrolylalkynones containing tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[g]indolyl moieties in the form of acylethynylcycloalka[b]pyrroles, resulting in a series of novel pyrrolo[1',2':2,3]imidazo[1,5-a]indoles and cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles with an acylethenyl group in up to an 81% yield. This original synthetic approach contributes to the arsenal of chemical methods promoting drug discovery.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Ludmila A. Oparina, Kseniya V. Belyaeva, Nikita A. Kolyvanov, Igor A. Ushakov, Maxim D. Gotsko, Lyubov' N. Sobenina, Alexander V. Vashchenko, Boris A. Trofimov
Summary: This study reports a novel reaction method in which Acylethynylpyrroles undergo facile catalyst-free annulation with 1-pyrrolines to afford acylmethylenetetrahydrodipyrrolo[1,2-a:1 ',2 '-c]imidazoles. The reaction achieves high yields and E-stereoselectivity of the olefin moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sofia O. Samultceva, Marina Yu Dvorko, Dmitrii A. Shabalin, Igor' A. Ushakov, Alexander V. Vashchenko, Elena Yu Schmidt, Boris A. Trofimov
Summary: 6-Methylene-5-oxaspiro[2.4]heptanones have been successfully synthesized via base-catalyzed dimerization of available alkynyl cyclopropyl ketones. The reaction proceeds at room temperature in the presence of the t-BuOK/t-BuOH/THF catalytic system, providing the desired spirocycles in a regio- and stereoselective manner. The study also demonstrates the wide synthetic utility of alkynyl cyclopropyl ketones as novel building blocks.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Organic
Dmitrii A. Shabalin
Summary: This review discusses the development of synthetic protocols for 2,4,6-triarylpyridines and emphasizes the utility and limitations of each method in the field of applied sciences.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
