Article
Chemistry, Physical
Lin-Jun Qi, Chong-Yang Shi, Peng-Fei Chen, Long Li, Gang Fang, Peng-Cheng Qian, Chao Deng, Jin-Mei Zhou, Long-Wu Ye
Summary: The study presents a novel gold-catalyzed 1,1-carboalkoxylation method for the synthesis of valuable cyclic compounds, enabling asymmetric synthesis through a chirality-transfer strategy. Further mechanistic insight into the distinct migration into gold carbenes is supported by theoretical calculations.
Article
Chemistry, Organic
Yong Xu, Jiangtao Sun
Summary: This study describes the use of gold-catalyzed cascade cyclization and 1,3-difunctionalization of 2-(1-alkyny)-2-alken-1-ones with N,O-acetals, leading to the discovery of novel 1,3-oxyaminomethylation and 1,3-aminomethylamination. By varying reaction conditions, particularly the gold catalysts, these two distinct reaction pathways can be selectively controlled. Tandem cyclization and 1,4-oxyaminomethylation have also been achieved.
Article
Chemistry, Organic
Lan Wei, Shiteng Ding, Mingqing Liu, Zongxiang Yu, Yuanjing Xiao
Summary: This study demonstrates that three types of trifluoromethylated pyrazolidines, pyrazolines, and pyrazoles can be synthesized by the divergent reaction of beta-CF3-1,3-enyne with various hydrazines.
Article
Chemistry, Applied
Junying Wang, Jianghui Du, Tao Wang
Summary: The synthesis of 2-aminopyrrolo[1,2-b]pyridazines from 1,3-diynamides and 1-aminopyrroles via gold(I)-catalyzed chemoselective hydroamination/hydroarylation cascade was successfully achieved. A total of 26 examples were conducted to investigate the substrate scope, and a plausible reaction mechanism was proposed. Moreover, the fluorescence properties of the resulting products in both solution and solid states were explored.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Shashank Shandilya, Manash Protim Gogoi, Shubham Dutta, Akhila K. Sahoo
Summary: Ynamide, a unique species with inherited polarization of nitrogen lone pair electron to triple bond, has been widely used for the development of novel synthetic methods and the construction of unusual N-bearing heterocycles. This review provides an overall scenic view into the gold catalyzed transformation of ynamides, including their reactivity towards various transfer reagents and carbon nucleophiles.
Article
Chemistry, Applied
Elisa Brambilla, Silvia Meraviglia, Edoardo Moneta, Donatella Nava, Silvia Rizzato, Giorgio Abbiati, Valentina Pirovano
Summary: A photoredox-promoted approach for the synthesis of [1,4]diazepino[1,7-a]indol-6(7H)-ones starting from N-indolyl phenylacrylamides and aroyl chlorides as radical source is reported. This method involves a cascade radical addition on C-C double bond followed by intramolecular cyclization at indole C2-position, resulting in the formation of two diastereomeric indole-fused 1,4-diazepinones characterized by a N-C(aryl) axial chirality, with yields ranging from 51% to 99%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Bo Zhu, Teng Sun, Zhi-Chao Chen, Lu Gao, Wei Du, Ying-Chun Chen
Summary: A substrate-controlled diversity-oriented approach using palladium catalysis was developed to access skeletally different frameworks. Various benzofulvenes were constructed in good yields, enantioselectivity, and E-selectivity via a cascade reaction. By modifying the vinyl substitutions of the substrate, formal 1-naphthylated amines were selectively obtained. Furthermore, the naphthalene products underwent a Diels-Alder cycloaddition reaction, leading to complex oxabicyclo[2.2.1]heptane architectures. This substrate-controlled strategy demonstrated great versatility in constructing structurally diverse compounds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jiayue Fu, Bingbing Li, Xiugui Wang, Qida Liang, Xiaoshi Peng, Lu Yang, Tao Wan, Xinxiu Wang, Bin Lin, Maosheng Cheng, Yongxiang Liu
Summary: In this study, a gold(I)-catalyzed 6-endo-dig cyclization of aromatic 1,5-enynes was developed to synthesize 2-(naphthalen-2-yl)anilines. The functional group tolerance of this cyclization was systematically examined, and a possible mechanism was proposed. Derivatization of 2-(naphthalen-2-yl)aniline was carried out to access benzo[alpha]carbazole, benzo[c,h]cinnoline and dibenzo[i]phenanthridine derivatives in a divergent manner.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Ruihan Yang, Danna Chen, Shiyi Lin, Xuege Yang, Lou Shi, Qiaowen Chang, Deqiang Liang
Summary: A visible light-induced perfluoroalkylative cyclization of 3-aza-1,5-dienes leading to pentasubstituted 1,3-dihydropyrrole-2-ones is demonstrated. The reaction is regiospecific, with the radical selectively adding across the acrylamido moiety. The enaminic double bond acts as a built-in radical trap. The method can be performed on a 2-gram scale using sunlight as the light source.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhenhua Xu, Ning Xian, Hongbiao Chen, Guo-Jun Deng, Huawen Huang
Summary: This study introduces a copper-based catalytic system for the efficient cyclization of methylketoximes and alkynals, offering a viable approach to synthesize 2-acylpyrroles with a broad range of compatible functionalities. Additionally, it suggests a key acyl migration mechanism that leads to the formation of N-acyl pyrroles or NH pyrroles by further hydrolysis, and also provides an opportunity for a three-component pyrrole assembly by simple addition of carboxylic acid.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Indre Misiunaite, Raminta Bajarunaite, Rita Buksnaitiene, Algirdas Brukstus, Ieva Zutaute
Summary: Electrophile-initiated nucleophilic cyclization of 2-alkynylthiobenzimidazoles is a useful tool for synthesizing new heterocyclic systems. However, halogen-initiated cyclization shows poor selectivity between electrophilic addition and substitution reactions using other imidazole analogues. In this research, different coinage metal catalysts were used to expand the scope of 7H-imidazo[2,1-b][1,3]thiazines in an atom-economic manner. Selective 6endo-dig pathway reactions were achieved in good to excellent yields using various 2-alkynylthioimidazoles with AuCl as the catalyst in DCE/DCM.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Ju Eun Jeon, Siyeon Jeong, Hayeon Kwak, Jung Min Joo
Summary: In this study, gold(III)-catalyzed cyclization reactions of alkynyl norbornene derivatives were developed to generate benzofused (hetero)arenes with substitutions at the benzocyclic ring. The combination of Au(OAc)(3) and AgNTf2 allowed for the annulation of (hetero)arenes by intramolecular hydro(hetero)arylation followed by retroDiels-Alder reactions to afford fully conjugated benzofused (hetero)arenes in higher yields than the previously developed Pd(OAc)(2)-catalyzed protocol. Additionally, using AuCl3 instead of Au(OAc)(3) led to a rearrangement of (hetero)arenes with the norbornene bridge installed at the more electron-rich and sterically demanding position to afford the corresponding regioisomeric products in a divergent manner. These results highlight the importance of steric effects in addition to the electronic effects of the catalyst and the substrate on the rearrangement.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Jingyu Zhang, Wei Xia, Meilin Qu, Saskia Huda, Jas S. Ward, Kari Rissanen, Markus Albrecht
Summary: The synthesis of novel N-fused polycyclic indolines was achieved through subsequent reduction and dearomatizing cyclization reactions, resulting in good yields of a broad variety of compounds including alkaloids such as indolines and phaithanthrin C.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Marc Devillard, Nour Nour Eddine, Marie Cordier, Gilles Alcaraz
Summary: A straightforward synthetic methodology for the preparation of photochromic siloles based on the dithienylethene motif has been developed. This method relies on an efficient palladium-catalyzed annulation reaction of a 2,3-bis(3-thienyl)-silirene with terminal alkynes in mild conditions. The reaction is functional group-tolerant and can be extended to the synthesis of photochromic polymers with different degrees of photochromic unit incorporation by adjusting the polymer/silirene stoichiometric ratio.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hai-xuan Liu, Fei Ji, Yu Chen, Ya Gao, Jun-ke Wang, Ming-zhi Zhang, Fang Liu, Qiang Sha
Summary: This study reports a divergent synthesis of a variety of 2 alpha- and 5 alpha-substituted furan derivatives from 2-hydroxy-1,4-diones, achieved through selective reactions using different substrates and catalysts. The products showed moderate antifungal activity against Rhizoctorzia solani and Botrytis cinerea.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemical Research Methods
Thi Yen Hang Bui, Peter Dedecker, Luc Van Meervelt
Summary: rsCherryRev1.4 is a reversibly photoswitchable variant of mCherry with improved properties compared to its precursor. The crystal structure of rsCherryRev1.4 revealed dimerization through disulfide bonding, which was strongly influenced by the presence of Cys24. This finding suggests the potential for developing redox sensors based on controlled dimerization in fluorescent proteins.
ACTA CRYSTALLOGRAPHICA SECTION F-STRUCTURAL BIOLOGY COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Thi Yen Hang Bui, Elke De Zitter, Benjamien Moeyaert, Ludovic Pecqueur, Bindu Y. Srinivasu, Anastassios Economou, Marc Fontecave, Luc Van Meervelt, Peter Dedecker, Branden Pedre
Summary: This article investigates the mechanism of fluorescence loss in the reversibly switchable monomeric Cherry (rsCherry) and its ancestor mCherry. It is found that the gradual loss of red fluorescence in the dark is caused by structural changes in the chromophore. This study provides new insights into a novel process occurring within fluorescent proteins, enhancing the chemical diversity and versatility of these molecules.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Physical
Yassine Laamari, Abdoullah Bimoussa, Mourad Fawzi, Ali Oubella, Taoufik Rohand, Luc Van Meervelt, My Youssef Ait Itto, Hamid Morjani, Aziz Auhmani
Summary: A series of novel compounds containing thymol were synthesized and their structures were confirmed. The compounds demonstrated moderate to high cytotoxicity against four human cancer cell lines. Particularly, compound 4b showed significant cytotoxicity and induced apoptosis in HT-1080 and A-549 cells. Evaluation techniques such as staining and flow cytometry were used to assess the effects on cell cycle and apoptosis.(c) 2023 Elsevier B.V. All rights reserved.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Felien Reniers, Stijn Anthonissen, Luc Van Meervelt, Wim Dehaen
Summary: This study presents a three-step synthetic pathway for the synthesis of fully decorated 8-azapurines, with a special focus on 6-alkyl derivatives. A diverse library of 8-azapurines was successfully obtained through interrupted CuAAC, oxidation, and cyclization reactions using various alkynes, azides, and amidines. Additionally, postfunctionalization reactions were demonstrated for selected substrates.
Article
Chemistry, Physical
Zhan Dong, Liangliang Song, Liang-An Chen
Summary: Asymmetric multicomponent reactions are efficient methods for constructing complex chiral molecules due to their step- and atom-economy. Nickel-catalyzed asymmetric three-component dicarbofunctionalization of alkenes has been well developed, and finds applications in total synthesis of natural products and late-stage modification of drugs. This concept summarizes the significant breakthroughs in this field, together with the related mechanisms, and highlights the remaining challenges and potential opportunities of multicomponent dicarbofunctionalization.
Article
Chemistry, Multidisciplinary
Chao Liu, Johan Van Der Eycken, Erik V. Van Der Eycken
Summary: A novel method was developed for transition metal-free N-S bond cleavage and subsequent C-N bond activation of Ugi-adducts. Diverse primary amides and a-ketoamides were prepared in a rapid, step-economic, and highly efficient manner in two steps. This strategy offers excellent chemoselectivity, high yield, and functional-group tolerance. Primary amides derived from the pharmaceuticals probenecid and febuxostat were successfully prepared. This method provides a new environmentally friendly pathway for the simultaneous synthesis of primary amides and a-ketoamides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Arina Y. Obydennik, Alexander A. Titov, Anna V. Listratova, Tatiana N. Borisova, Irina L. Sokolova, Victor B. Rybakov, Erik V. Van der Eycken, Leonid G. Voskressensky, Alexey V. Varlamov
Summary: In this study, 1-substituted 1-ethynyl-2-vinyldi- and tetrahydroisoquinolines were successfully subjected to [3,3]-sigmatropic rearrangement under microwave irradiation at 150 degrees Celsius in toluene, in the presence of nucleophiles (DMAP, triphenylphosphine and tetrahydrothiophene), yielding pyrrolo[2,1-b][3]benzazepines with good yields. The replacement of toluene with acetonitrile directed the rearrangement towards the formation of 7,11b-dihydro-6H-pyrido[2,1-a]isoquinolines.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Materials Science, Multidisciplinary
Jianjun Huang, Flip de Jong, Davita Martina Elisa van Raamsdonk, Jonathan Vandenwijngaerden, Akane Inoue, Daniel Escudero, Luc Van Meervelt, Mark van der Auweraer, Wim Dehaen
Summary: A new family of unsymmetrical boron chromophores, BOPAM, has been developed through a one-pot, three-step reaction with high efficiency and broad substrate tolerance. Some of the BOPAM dyes exhibit interesting photophysical properties with fluorescence quantum yields up to 0.98 in toluene. Tailored molecular design guided by computational investigations allows precise tuning of their emissive properties.
ADVANCED OPTICAL MATERIALS
(2023)
Review
Chemistry, Organic
Alisa A. Nevskaya, Anna D. Zinoveva, Erik V. van der Eycken, Leonid G. Voskressensky
Summary: This paper provides a review on the synthesis methodologies and applications of different indolizine derivatives, including thienoindolizines and indolizino[8,7-b]indoles. Indolizine nucleus is a privileged scaffold of various natural and synthetic molecules with significant biological activity. Fused-indolizines, such as thienoindolizines and indolizinoindoles, have attracted great interest due to their antitumor, antimicrobial, and enzyme inhibitor activity. The study summarizes the approaches to the synthesis, properties, and application of various indolizine derivatives, with a focus on recent articles on indolizines and indolizino[8,7-b]indoles, as well as a general review on thienoindolizine derivatives.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Nadeem Abad, Fares Hezam Al-Ostoot, Sajda Ashraf, Karim Chkirate, Majed S. Aljohani, Hussam Y. Alharbi, Shafeek Buhlak, Mohamed El Hafi, Luc Van Meervelt, Basheer M. Al-Maswari, El Mokhtar Essassi, Youssef Ramli
Summary: Drug design is a constantly evolving field where researchers strive to improve their understanding of molecular interactions and develop innovative techniques for creating effective and safe medications. This article reports the synthesis and characterization of a novel triazolequinoxalin molecule (TZQ) through various spectroscopic and crystallographic methods.
Article
Crystallography
Hai Le Thi Hong, Thao Le Phuong, Thong Van Pham, Hue Minh Thi Nguyen, Luc Van Meervelt
Summary: （English Summary:）
The molecular and crystal structures of (E)-2-[(benzo[d]thiazol-2-ylimino)methyl]-5-(diethylamino)-phenol and its unexpected reaction product with triphenylborane are described. The absorption and emission properties of these compounds as well as their aggregation-induced emission properties are discussed.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2023)
Review
Chemistry, Multidisciplinary
Liangliang Song, Lingchao Cai, Lei Gong, Erik V. Van der Eycken
Summary: Copper-catalyzed enantioselective coupling reactions have been extensively studied for the rapid synthesis of chiral molecules. Despite progress in polar and radical mechanisms, the development of general and practical strategies for the regio-, enantio-, and diastereoselective assembly of stereogenic centers remains challenging. The integration of photocatalysis with asymmetric copper catalysis offers new reaction pathways and diverse chiral compounds, expanding the scope of radical chemistry. This review provides a summary of recent advances in photoinduced copper-catalyzed enantioselective coupling reactions, with a discussion on the mechanistic aspects.
CHEMICAL SOCIETY REVIEWS
(2023)
Review
Chemistry, Multidisciplinary
Alexey A. Festa, Olga A. Storozhenko, Leonid G. Voskressensky, Erik V. van der Eycken
Summary: The use of visible light-promoted chemistry in halogenation and halofunctionalisation reactions has significant impact.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: In this study, a metal-free cascade cyclization method was developed for the construction of structurally novel polyheterocycles. The approach involves the use of a hypervalent iodine(iii) reagent and generates diverse N-O fused spiro polyheterocycles in high yields. The synthesized compounds exhibit good antifungal activity against crop and forest pathogenic fungi, with one compound showing superior performance compared to the positive control.
ORGANIC CHEMISTRY FRONTIERS
(2023)
