Article
Chemistry, Organic
Lili Han, Mengmeng Huang, Yabo Li, Jianye Zhang, Yu Zhu, Jung Keun Kim, Yangjie Wu
Summary: An electrolyte- and catalyst-free electrooxidative approach was investigated to produce sulfonylated imidazo[1,2-a]pyridines, achieving high yields. The proposed reaction mechanism might occur via a radical process, with the spectral properties of imidazo[1,2-a]pyridines potentially controlled by modifying their 8-position.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Sajjad Azizi, Nasrin Shadjou, Jafar Soleymani
Summary: An innovative leach-proof nanocatalyst CuI/Fe(3)O(4)NPs@IL-KCC-1 with exceptional dendritic fibrous structure and ionic liquid groups showed high catalytic activity in aqueous media, could be easily recovered by an external magnet, recycled for multiple cycles, and achieved high yields without the need for a chromatographic column.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Javeed Ahmad Tali, Ravi Shankar
Summary: Here, we report an unprecedented protocol using ruthenium-catalyzed annulation for the synthesis of 6H-chromeno[4 ',3 ':4,5]imidazo[1,2-a]pyridin-6-one, and a new method for intramolecular chelation-assisted C-H activation to produce functionalized 2-(3-formylimidazo[1,2-a]pyridin-2-yl)phenyl acetate. Furthermore, a one-pot approach using ruthenium catalysis and formic acid has been developed for the gram-scale synthesis of bis(2-phenylimidazo[1,2-a]pyridin-3yl)methane (BIP) and the late-stage functionalization of zolimidine, a marketed drug, with good yield.
Article
Chemistry, Organic
Frederic Vuillermet, Joanick Bourret, Guillaume Pelletier
Summary: The study describes a new method for the synthesis of imidazo[1,2-a]pyridines through the reaction between 2-chloropyridines and 2H-azirines, which involves the formation of electrophilic trifloyl-aziridin-2-yl triflate species and transient pyridinium salts. Thorough optimization of the activation/cyclization process resulted in selective formation of C3-substituted imidazo[1,2-a]pyridines with yields ranging from 15% to 85% for a variety of substituted heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jingyun Zhu, Ziyue Chen, Meng He, Daoxin Wang, Liangsen Li, Junchao Qi, Renyi Shi, Aiwen Lei
Summary: The study developed an efficient and metal-free synthesis method for the production of biologically and synthetically useful compounds. The reaction exhibited high yields, and the scaled-up experiment resulted in an ideal yield of the desired product.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Chun-Hua Ma, Ming Chen, Zhi-Wen Feng, Yan Zhang, Jin Wang, Yu-Qin Jiang, Bing Yu
Summary: This review summarizes recent advances in radical reactions for the direct functionalization of imidazo[1,2-a]pyridines through transition metal catalysis, metal-free oxidation, and photocatalysis strategies.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Ting Cui, Yanling Zhan, Changhui Dai, Jun Lin, Ping Liu, Peipei Sun
Summary: An electrochemical oxidative regioselective C-H cyanation of imidazo[1,2-a]pyridines was developed utilizing TMSCN as the cyano source, with the KH2PO4/K2HPO4 buffer being essential for the transformation. This protocol was compatible with a broad range of substituted imidazo[1,2-a]pyridines and provided the C3 cyanated products in moderate to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yong Yuan, Zhilin Zhou, Lin Zhang, Liang-Sen Li, Aiwen Lei
Summary: The electrochemical oxidative C3 acyloxylation of imidazo[1,2-alpha]pyridines was demonstrated for the first time, showing that it can be carried out under mild conditions and is applicable to alkyl carboxylic acids as well as aromatic carboxylic acids.
Article
Multidisciplinary Sciences
Sepideh Bibak, Ahmad Poursattar Marjani
Summary: In this research, a magnetically separable heterogeneous nanocatalyst named Fe3O4@CPTMO@dithizone-Ni was synthesized using a core-shell procedure. The catalyst showed high stability and recyclability with excellent performance in the green synthesis of 4H-benzo[h]chromenes. It possesses advantages such as easy separation, cost-effectiveness, and environmental friendliness.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Medicinal
Uttam B. Karale, Akash U. Shinde, Dattatraya A. Babar, Komal G. Sangu, Siva Krishna Vagolu, Vamshi K. Eruva, Surender S. Jadav, Sunil Misra, Sriram Dharmarajan, Haridas B. Rode
Summary: A series of 3-aryl-substituted imidazo[1,2-a]pyridines were synthesized through direct arylation, with compound 26 identified as a potent antituberculosis lead against Mycobacterium tuberculosis H37Rv. Compound 26 showed significant π-π interactions with the Tyr389 and Trp312 residues of Mtb QcrB in the active site of the M. tuberculosis cytochrome bc1 complex.
ARCHIV DER PHARMAZIE
(2021)
Article
Chemistry, Multidisciplinary
Zitong Zhou, Danyang Luo, Guanrong Li, Zhongtao Yang, Liao Cui, Weiguang Yang
Summary: An efficient and simple three-component cascade reaction was reported, providing a variety of polysubstituted imidazo[1,2-a]pyridine derivatives in moderate to excellent yields. The reaction proceeds through a CuAAC/ring-cleavage process and forms a highly active intermediate alpha-acyl-N-sulfonyl ketenimine without the need for a base.
Article
Chemistry, Multidisciplinary
Vanya Kurteva
Summary: This Mini-Review highlights the most effective protocols for metal-free direct synthesis of imidazo[1,2-a]pyridines, crucial target products and key intermediates, developed in the past decade, emphasizing the ecological impact of the methods and the mechanistic aspects. The procedures efficiently applied in the preparation of important drugs and promising drug candidates are also underlined.
Article
Chemistry, Organic
Yinrong Wu, Lu Li, Kangmei Wen, Jie Deng, Jiewen Chen, Jie Shi, Ting Wu, Jianxin Pang, Xiaodong Tang
Summary: A copper-catalyzed C-3 functionalization of imidazo[1,2-a]pyridines with 3-indoleacetic acids has been developed, providing a series of compounds with potent antiproliferative activity in cancer cell lines under simple reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ilya P. Filippov, Anastasiya Agafonova, Gleb D. Titov, Ilia A. Smetanin, Nikolai Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: An efficient one-pot synthesis method for imidazo[1,2-a]pyridines has been developed, which involves the construction of the bicyclic framework of imidazo[1,2-a]pyridines in two steps. The method can also be used for the synthesis of imidazo[2,1-a]isoquinolines. Stable tetrafluoroborates were obtained by converting the unstable (2H-azirin-2-yl)pyridinium/isoquinolinium bromides, which can be cyclized to imidazo[1,2-a]pyridines under UV irradiation in the presence of bromide ions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Javeed Ahmad Tali, Gulshan Kumar, Bhupesh Kumar Sharma, Younis Rasool, Yashika Sharma, Ravi Shankar
Summary: Imidazo[1,2-a]pyridine has potent medicinal properties and has attracted much interest in drug development. This review provides an overview of the outcomes obtained in the field of global ring functionalization, focusing on the functionalization reactions at each carbon atom.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Rahman Hosseinzadeh, Fatemeh Fathalipour, Mahmood Tajbakhsh, Mohammad Mavvaji, Mona Pooryousef
Summary: In this study, a mild and efficient one-pot synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via a three-component reaction under ball-milling conditions was reported. The optimized reaction conditions yielded a wide variety of derivatives in high yields, offering advantages such as high product yields, short reaction time, and simple work-up procedure.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Ghazaleh Zarrinzadeh, Mahmood Tajbakhsh, Rahman Hosseinzadeh, Mohammad A. Khalilzadeh, Masoumeh Hosseinzadeh
Summary: In this study, the binding affinities and interaction modes between Euparin derivatives and N-myristoyltransferase enzyme were evaluated through molecular docking studies. Compounds 1-3 exhibited significant hydrophobic and hydrogen bonding interactions with important residues at the active site of the receptor. Among them, compound 1 showed the highest antifungal activity, compound 2 displayed cytotoxicity against a cancer cell line, and compound 3 exhibited strong growth inhibition against a bacterial strain.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Inorganic & Nuclear
Rahman Hosseinzadeh, Nora Aghili, Mohammad Mavvaji
Summary: Functionalized nanocellulose was used to prepare a heterogeneous copper catalyst, which showed remarkable catalytic efficiency in C-O and C-N cross-coupling reactions. The catalyst could be easily recovered and reused multiple times without significant loss of catalytic activity.
Article
Chemistry, Multidisciplinary
Sahar Peiman, Robabeh Baharfar, Rahman Hosseinzadeh
Summary: In this paper, a nanocatalyst (Fe3O4@SiO2@DNHCS-Tr@CuI) containing PAMAM dendrimer and trypsin enzyme supported on magnetic nanosilica with immobilized CuI NPs was prepared. The nanocatalyst was characterized using various techniques and showed highly efficient catalytic activity for the synthesis of propargylamines in green conditions, with high yields, short reaction times and easy separation and recovery of the catalyst for further use.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Applied
Golnaz Rahimzadeh, Mahmood Tajbakhsh, Mansoureh Daraie, Masoud Mohammadi
Summary: In this study, a complex of dysprosium and balsalazide was trapped between the functionalized g-C3N4 and halloysite to form a heterogenized catalytic complex for the synthesis of biologically active pyran derivatives with high yields. The catalyst showed excellent reusability for up to 8 cycles without leaching of metal during the reaction, indicating its heterogeneous nature.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Maryam Abaszadeh, Rahman Hosseinzadeh, Mahmood Tajbakhsh, Shahram Ghasemi
Summary: Magnetic graphene oxide (MGO) was functionalized with 5-amino-1,10-phenanthroline (APhen) to obtain MGO@APhen. The results showed that MGO@APhen acts as an efficient heterogeneous catalyst in the C-N coupling reaction of aryl halides with amides and N-heterocycles in the presence of CuI. Additionally, MGO@APhen demonstrated excellent performance in the adsorption of heavy metal ions.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Applied
Mohammadreza Azizi Amiri, Ghasem Firouzzadeh Pasha, Mahmood Tajbakhsh, Sakineh Asghari
Summary: The nano NaY zeolite-supported copper-amine complex was prepared and its catalytic activity was studied. Various techniques were used to characterize the structure of the synthesized catalyst. The results showed that the catalyst exhibited high reaction yields and could be reused multiple times. The supported amine improved the catalytic activity of the zeolite and enhanced its coordination capability with copper ions. This environmentally benign method can be used to prepare other beneficial heterocyclic compounds.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Taraneh Abbaspour, Ghasem Firouzzadeh Pasha, Mahmood Tajbakhsh
Summary: An efficient acid-catalyzed synthesis of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones is reported using a novel polymer catalyst, which can be easily regenerated and reused. The catalyst was characterized using various analytical techniques, and it showed high product yield and a simple work-up procedure.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Hamidreza Younesi, Sakineh Asghari, Ghasem Firouzzadeh Pasha, Mahmood Tajbakhsh
Summary: In this study, a multi-component reaction was used to modify the surface of nano zeolite, resulting in high functionality. The Ugi reaction was applied for the first time to develop a hydrogen-bonding nanocatalyst by post-modifying nano NaY zeolite with 3-aminopropyltriethoxysilane (APTES) and then reacting it with salicylaldehyde, tert-butyl isocyanide, and acetic acid. The modified nano zeolite showed improved reactivity, dispersibility, and hydrogen bonding formation capability. The nanocatalyst was characterized using various techniques and exhibited excellent catalytic activity in a three-component reaction. The catalyst could be easily separated and reused multiple times without significant activity loss, making this eco-friendly method suitable for the preparation of other important heterocyclic compounds.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Ehsan Roustaie, Mahmood Tajbakhsh, Rahman Hosseinzadeh
Summary: Zinc oxide was supported on the surface of ZSM-5 zeolite using the extract of Convolvulus persicus to create a stable nanocatalyst, ZnO/ZSM-5. The catalyst exhibited good catalytic behavior in the Biginelli reaction, producing high yields of products and allowing for easy recovery and reusability.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ali Zamani, Yaghoub Sarrafi, Mina Roustaei Rouzbahani, Mahmood Tajbakhsh
Summary: A new indole-containing 2,6-pyridinedicarbohydrazide P3 was synthesized and characterized as an efficient fluorescent turn-off and colorimetric cation receptor. The P3 receptor demonstrated a rapid color change and selective fluorescence quenching in the presence of Cu2+ cations. The compound showed potential as a Cu2+ test kit with high sensitivity and a low limit of detection.
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Ghazaleh Zarrinzadeh, Mahmood Tajbakhsh, Rahman Hosseinzadeh, Zahra Ghanbarimasir, Maryam Roudbary, Mojtaba Mohseni, Hamid Nadri
Summary: Euparin and 2-hydroxy acetophenone hydrazone derivatives (2-7) were synthesized and characterized. Their inhibitory potential on AchE enzyme was determined using a modified spectrophotometric approach. Compounds 3, 5, and 7 showed strong and specific inhibition of AchE. Docking tests confirmed the interactions between these compounds and AchE. Compound 7 exhibited the highest AchE inhibitory activity and docking score compared to the reference drug, Donepezil.
JOURNAL OF MOLECULAR STRUCTURE
(2023)