Article
Chemistry, Multidisciplinary
J. Daniel Bailey, Edward Helbling, Amey Mankar, Matthew Stirling, Fred Hicks, David K. Leahy
Summary: Reducing or eliminating organic solvent use in pharmaceutical manufacturing is a highly effective way to reduce environmental, health, and safety impacts. The process described utilizing primarily water-based methods significantly reduces material inputs and organic solvent use, while surprisingly using less water and improving overall yield compared to traditional methods.
Article
Chemistry, Multidisciplinary
Jade Dussart-Gautheret, Julie Yu, Krithika Ganesh, Gaikwad Rajendra, Fabrice Gallou, Bruce H. Lipshutz
Summary: This study describes the surfactant-enabled asymmetric ATA-catalyzed reductive aminations in water, which enhance the conversion levels and enable 1-pot chemoenzymatic catalysis. The modified conditions involving both biocatalysis and chemocatalysis are environmentally responsible, indicating the potential of using chemistry in water.
Article
Chemistry, Multidisciplinary
Matthias Elfinger, Timon Schoenauer, Sabrina L. J. Thomae, Robert Staeglich, Markus Drechsler, Mirijam Zobel, Juergen Senker, Rhett Kempe
Summary: The 3D metal catalyst developed here utilizes hydrogen as the reducing agent and easily handled ammonia dissolved in water as the nitrogen source for the synthesis of primary amines. The catalyst operates under mild conditions and outperforms commercially available noble metal catalysts. The key to its high activity is the unique support material it uses.
Article
Chemistry, Organic
Hao Song, Yao Xiao, Zhuohua Zhang, Wanjin Xiong, Ren Wang, Liangcheng Guo, Taigang Zhou
Summary: A new synthetic method for the selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines has been developed. The method demonstrates high selectivity and yields up to 95%, and has been successfully applied in the synthesis of N-15 labeled compounds with an 89% yield.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Vinothkumar Vinayagam, Tanguturi Venkatanarayana Hajay Kumar, Ravi Nune, Satish Kumar Karre, Subir Kumar Sadhukhan
Summary: We developed a one-step procedure for selectively reducing secondary and tert-amides to their corresponding amine derivatives in the presence of an ester. This reaction was achieved by combining photoredox, nickel catalysis, and phenyl silane as a reductant under blue LED light (455 nm) at room temperature. Furthermore, this mild light-promoted dual metallaphotoredox catalytic system was effective in selectively reducing lactam to cyclic amines without affecting the ester moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mujeeb A. Sultan, Renjith Raveendran Pillai, Eman Alzahrani, Ahmed A. Alsofi, Sadam A. Al-Qadhi, Rami Adel Pashameah
Summary: In this study, a maprotiline analog was synthesized and its structure was elucidated using NMR and mass spectrometry techniques. Density functional theory calculations and molecular docking simulations showed that the synthesized compounds have good antidepressant activities, making them potential candidates for antidepressant drugs.
JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Xinmin Li, Yue Hu, Asma M. Alenad, Bei Zhou, Zhuang Ma, Jie Gao, Rajenahally V. Jagadeesh, Matthias Beller
Summary: A mild and convenient protocol for the synthesis of diverse secondary and tertiary amines, as well as N-methylated products, is presented. This protocol works efficiently at room temperature using ammonia borane as the reductant and is applicable to a wide range of substrates, including chiral amines and amino acid derivatives. The utility of this methodology is demonstrated by gram-scale reactions and selected synthesis of drug molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Matthieu Jouffroy, Thi-Mo Nguyen, Marie Cordier, Marielle Blot, Thierry Roisnel, Rafael Gramage-Doria
Summary: Direct reductive amination (DRA) is a widely used reaction in organic chemistry, aiming to convert carbonyl groups and amines into aminated compounds. The conventional method involves the use of a super stoichiometric amount of hazardous hydride reagents, which is incompatible with many sensitive functional groups. This study presents a new DRA method using iridium catalysis, overcoming the limitation of ketones with 2 degrees amines.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Romana Micova, Zuzana Bielkova, Cyril Rajnak, Jan Titis, Milan Gembicky, Franz Renz, Ondrej Malina, Erika Samolova, Jana Novacikova, Roman Boca
Summary: A new series of Fe(III) mononuclear complexes have been prepared and characterized. The magnetic data shows significant differences among different substances, and the zero-field splitting has been described.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xue-Rui Tian, Zhi-Yu Jiang, Sheng-Li Hou, Han-Shi Hu, Jun Li, Bin Zhao
Summary: A stable metal-organic framework (MOF) was synthesized and exhibited excellent catalytic performance in the reductive amination of aldehydes with DMF, with high stability and reusability.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Risto Savela, Nataliya D. Shcherban, Marko M. Melander, Igor Bezverkhyy, Irina L. Simakova, Otto Langvik, Ekaterina Kholkina, Tamara Schindler, Annabelle Krauss, Karoliina Honkala, Dmitry Yu Murzin, Reko Leino
Summary: Selective hydrogenation of unsaturated imines over heterogeneous catalysts, specifically with iridium on carbon nitrides and amphoteric metal oxides in toluene solvent, provides the best selectivity towards unsaturated amines. This study demonstrates a promising catalytic performance and chemoselectivity, which has not been reported before, under atmospheric hydrogen pressure and low temperatures.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Organic
Dusty Cadwallader, Tristan R. Tiburcio, George A. Cieszynski, Christine M. Le
Summary: This article introduces a method for synthesizing carbamoyl fluorides, which uses inexpensive and easily accessible starting materials, avoids the use of light-, temperature-, and moisture-sensitive chemicals, and has practical advantages over existing methods.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Peiyuan Yao, James R. Marshall, Zefei Xu, Jesmine Lim, Simon J. Charnock, Dunming Zhu, Nicholas J. Turner
Summary: In this study, a new stereoselective biocatalytic synthesis method for N-substituted alpha-amino esters was reported, utilizing diverse metagenomic imine reductases. Both enantiomers of the target products were synthesized with high conversion and excellent enantioselectivity under mild reaction conditions. Furthermore, over 20 different preparative scale transformations were performed, demonstrating the scalability of this system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Weixi Kong, Yunting Liu, Chen Huang, Liya Zhou, Jing Gao, Nicholas J. Turner, Yanjun Jiang
Summary: We report the engineering of an amine dehydrogenase (AmDH) from Jeotgalicoccus aerolatus for the direct asymmetric reductive amination of heteroaryl ketones. The engineered enzyme exhibited excellent conversions and enantioselectivities, even for ketones with bulky alkyl chains. Directed evolution based on molecular docking was used to enhance the enzyme's activity by enlarging the active pocket with a more hydrophobic entrance. The engineered enzyme was also applied in the synthesis of pharmaceutically relevant amines and a key intermediate of chiral pincer ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Itziar Penafiel, Robert A. W. Dryfe, Nicholas J. Turner, Michael F. Greaney
Summary: The integration of electro and bio-catalysis offers new ways of making molecules under very mild, environmentally benign conditions. The combined process offers a new approach to amine alkylation with native alcohols, a key bond formation in the chemical economy that is currently achieved via precious metal-catalyzed hydrogen-borrowing technologies.
Article
Engineering, Electrical & Electronic
Seyed Mohammad Javad Nabavi, Heshmatollah Alinezhad, Behzad Hosseinzadeh, Raheleh Ghahary, Mahmood Tajbakhsh
JOURNAL OF ELECTRONIC MATERIALS
(2020)
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)
Review
Chemistry, Medicinal
Fatemeh Salehian, Hamid Nadri, Leili Jalili-Baleh, Leila Youseftabar-Miri, Syed Nasir Abbas Bukhari, Alireza Foroumadi, Tuba Tuylu Kucukkilinc, Mohammad Sharifzadeh, Mehdi Khoobi
Summary: The combination of heterocycles offers a new opportunity to create novel multicyclic compounds with improved biological activity, and 3,4-heterocycle-fused coumarins have shown outstanding potential in the field of biological activity.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Applied
Raheleh Razavian Mofrad, Hassan Kabirifard, Mahmood Tajbakhsh, Ghasem Firouzzadeh Pasha
Summary: The efficient base-catalyzed synthesis of dihydropyrimidines and N-acetyl pyrazoles using 1-(2-aminoethyl)piperazine-modified nano-NaY zeolite (ZeSi-AP) offers a green and mild approach with a straightforward work-up procedure. The heterogeneous catalyst shows benefits of high product yield and easy regeneration for at least four cycles without losing activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
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, Multidisciplinary
Reza Yousefi, Abolfazl Hosseini, Mahmood Tajbakhsh
Summary: A new system using copper nanoparticles catalyzes the decarboxylation of aromatic carboxylic acids under amine-free conditions. Ortho-substituted benzoic acids with electron-deficient and electron-rich groups show effective decarboxylation, while meta- and para-substituted benzoic acids have lower reactivity and moderate yields of decarboxylated products.
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)
Article
Biology
Zari Fallah, Hossein Nasr Isfahani, Mahmood Tajbakhsh, Mojtaba Mohseni, Ebrahim Zabihi, Zeinab Abedian
Summary: The triazole functionalized cyclodextrin and cyclodextrin-triazole-titanium based nanocomposite exhibited strong antibacterial activity against both gram positive and gram negative bacteria. Additionally, the cytotoxicity of CD.COM was found to inhibit the growth of cancer cells in a dose and time dependent manner, while having no significant effect on normal cells.
BRAZILIAN ARCHIVES OF BIOLOGY AND TECHNOLOGY
(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)
