TY - JOUR AU - Kurtán, Tibor AU - Szántay, Csaba (Ifj.) AU - Gottsegen, Ágnes AU - Kálai, Tamás AU - Faigl, Ferenc AU - Bombicz, Petra TI - Tudományos Ülés Antus Sándor emlékére JF - MAGYAR KÉMIKUSOK LAPJA J2 - MAGY KEM LAP VL - 77 PY - 2022 IS - 9 SP - 276 EP - 278 PG - 3 SN - 0025-0163 UR - https://m2.mtmt.hu/api/publication/33549226 ID - 33549226 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Hergert, Tamás AU - Mátravölgyi, Béla AU - Örkényi, Róbert Zoltán AU - Éles, János AU - Faigl, Ferenc TI - Multistep batch-flow hybrid synthesis of a terbinafine precursor JF - JOURNAL OF FLOW CHEMISTRY J2 - J FLOW CHEM VL - 12 PY - 2022 IS - 1 SP - 51 EP - 57 PG - 7 SN - 2062-249X DO - 10.1007/s41981-021-00188-9 UR - https://m2.mtmt.hu/api/publication/32384665 ID - 32384665 N1 - Funding Agency and Grant Number: Budapest University of Technology and Economics Funding text: Open access funding provided by Budapest University of Technology and Economics. AB - A three-step batch-flow hybrid process has been developed for an expeditious synthesis of the enynol key intermediate of antifungal terbinafine. This procedure involves consecutive organometallic steps without the necessity of any in-line purification: after a metalation by n-butyllithium, a selective addition of the lithium salt was elaborated followed by a Grignard reaction resulting in a high yield of 6,6-dimethylhept-1-en-4-yn-3-ol. Moreover, as an alternative to tetrahydrofuran, cyclopentyl methyl ether was used as solvent implementing a safe, sustainable, yet selective synthetic process. Even on a laboratory-scale, the optimized batch-flow hybrid process had a theoretical throughput of 41 g/h. Furthermore, the newly developed process provides an efficient synthesis route to the key-intermediate, while making acrolein obsolete, minimizing side-products, and enabling safe and convenient scale-up. LA - English DB - MTMT ER - TY - JOUR AU - Kovács, Ervin AU - Faigl, Ferenc AU - Mucsi, Zoltán TI - Regio- and Diastereoselective Synthesis of 2-Arylazetidines. Quantum Chemical Explanation of Baldwin’s Rules for the Ring-formation Reactions of Oxiranes. JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 85 PY - 2020 IS - 17 SP - 11226 EP - 11239 PG - 17 SN - 0022-3263 DO - 10.1021/acs.joc.0c01310 UR - https://m2.mtmt.hu/api/publication/31401582 ID - 31401582 LA - English DB - MTMT ER - TY - JOUR AU - Szabó, Balázs Péter AU - Szakter, Kiara AU - Thurner, Angelika AU - Faigl, Ferenc AU - Éles, János AU - Greiner, István TI - A Novel, Domino Synthesis of Tricyclic Benzimidazole Derivatives Using Continuous Flow JF - PERIODICA POLYTECHNICA-CHEMICAL ENGINEERING J2 - PERIOD POLYTECH CHEM ENG VL - 64 PY - 2020 IS - 1 SP - 1 EP - 8 PG - 8 SN - 0324-5853 DO - 10.3311/PPch.14275 UR - https://m2.mtmt.hu/api/publication/31084985 ID - 31084985 AB - A novel method for synthesis of tricyclic benzimidazole derivatives by using continuous flow reactor is reported. Disadvantages of the well-known batch methods have been avoided utilizing the flow chemistry technology. Beside the one pot reductive cyclization using H-Cube Pro (R), the dehydration step was also optimized producing the desired lactam compounds. Then the acylation was optimized under microwave conditions and that reaction was also integrated into the flow system using an Asia heater module. This acylation dramatically reduced the reaction time under continuous-flow conditions, with a residence time of 30 min. LA - English DB - MTMT ER - TY - BOOK AU - Hergert, Tamás AU - Mátravölgyi, Béla AU - Szabó, B. AU - Faigl, Ferenc AU - Éles, J. AU - Greiner, István TI - A Multistep Flow Synthesis of the Key Intermediate of Terbinafine PY - 2019 UR - https://m2.mtmt.hu/api/publication/31159670 ID - 31159670 LA - English DB - MTMT ER - TY - BOOK AU - Hergert, Tamás AU - Faigl, Ferenc AU - Mátravölgyi, Béla TI - Pyrroloindolones as a Versatile Buildig Block: A Syntethic Study and Application PY - 2019 UR - https://m2.mtmt.hu/api/publication/31159620 ID - 31159620 LA - English DB - MTMT ER - TY - BOOK AU - Hergert, Tamás AU - Posta, T. AU - Faigl, Ferenc AU - Mátravölgyi, Béla TI - A Stereodivergent Access to 2-Alkenylated Indoles PY - 2019 UR - https://m2.mtmt.hu/api/publication/31159603 ID - 31159603 LA - English DB - MTMT ER - TY - JOUR AU - Kovács, Ervin AU - Huszka, Balázs AU - Gáti, Tamás AU - Nyerges, Miklós AU - Faigl, Ferenc AU - Mucsi, Zoltán TI - Chemoselective Strategy for the Direct Formation of Tetrahydro-2,5-methanobenzo[c]azepines or Azetotetrahydroisoquinolines via Regio- and Stereoselective Reactions JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 84 PY - 2019 IS - 11 SP - 7100 EP - 7112 PG - 13 SN - 0022-3263 DO - 10.1021/acs.joc.9b00798 UR - https://m2.mtmt.hu/api/publication/30786305 ID - 30786305 AB - The present study reports regio- and highly diastereoselective preparative methods for the synthesis of versatile alkaloid-type compounds from oxiranylmethyl tetrahydroisoquinolines. 2,5-Methanobenzo[c]azepines or azetidine-fused heterocycles were synthesized in tandem reactions depending on the absence or presence of a BF3 co-reagent. A high functional group tolerance has also been demonstrated. DFT calculations with an explicit solvent model confirmed the proposed reaction mechanisms and the role of kinetic controls on the stereochemical outcome of the reported new methods. LA - English DB - MTMT ER - TY - JOUR AU - Szabó, Balázs Péter AU - Tamás, Bálint AU - Faigl, Ferenc AU - Éles, János AU - Greiner, István TI - Diastereoselective synthesis of cis-N-Boc-4-aminocyclohexanol with reductive ring opening method using continuous flow JF - JOURNAL OF FLOW CHEMISTRY J2 - J FLOW CHEM VL - 9 PY - 2019 IS - 1 SP - 13 EP - 17 PG - 5 SN - 2062-249X DO - 10.1007/s41981-018-00028-3 UR - https://m2.mtmt.hu/api/publication/30415639 ID - 30415639 AB - The N-protected cis-4-aminocyclohexanol derivatives have proven to be valuable intermediates in the syntheses of active pharmaceutical ingredients (APIs). A novel continuous flow process for hydrogenation of N-protected 2-oxa-3-azabicyclo[2.2.2]oct-5-ene cycloadducts to the corresponding cis-4-aminocyclohexanols has been reported using H-Cube Pro. A > 99% selectivity towards the desired product was obtained using Raney nickel catalyst cartridge. Under carefully selected hydrogenation parameters the reduction could stop at the also valuable 2-oxa-3-azabicyclo[2.2.2] octane intermediate, with a selectivity of >99%. The N-protected 2-oxa-3-azabicyclo[2.2.2]oct-5-ene producing nitroso hetero-Diels–Alder cycloaddition was also accomplished in a flow system using an Omnifit column packed with MnO2. The two flow reactions were successfully merged in a system, thus the product was obtained in a multistep flow synthesis without any isolation or purification steps. Compared with the previously reported batch processes, the present multistep procedure facilitates an efficient cis selective preparation of numerous synthetically valuable 4-aminocyclohexanol derivatives. LA - English DB - MTMT ER - TY - BOOK AU - Hergert, Tamás AU - Faigl, Ferenc AU - Mátravölgyi, Béla TI - Synthesis of Fluorazone via Tf2O-mediated Cyclizations and their One-pot Copper(I) Chloride Co-catalyzed SM Coupling Reactions PY - 2018 UR - https://m2.mtmt.hu/api/publication/31159558 ID - 31159558 LA - English DB - MTMT ER -