TY - JOUR AU - Shahmohammadi, Sayeh AU - Orsy, György AU - Forró, Enikő TI - Lipase-catalyzed Strategies for the Preparation of Key Intermediates for the Synthesis of the Taxol Side Chain JF - MINI-REVIEWS IN ORGANIC CHEMISTRY J2 - MINI-REV ORG CHEM VL - 23 PY - 2026 IS - 1 SP - 1 EP - 9 PG - 9 SN - 1570-193X DO - 10.2174/0118756298317278240913071521 UR - https://m2.mtmt.hu/api/publication/36203475 ID - 36203475 LA - English DB - MTMT ER - TY - JOUR AU - Mándoki, András AU - Orsy, György AU - Pászti, Zoltán AU - Porcs-Makkay, Márta AU - Bogdán, Dóra AU - Simig, Gyula AU - Mándity, István AU - Volk, Balázs TI - Continuous-flow regioselective reductive alkylation of oxindole with alcohols and aldehydes in a fast and economical manner JF - SYNTHESIS-STUTTGART J2 - SYNTHESIS-STUTTGART VL - 55 PY - 2023 IS - 23 SP - 4025 EP - 4033 PG - 9 SN - 0039-7881 DO - 10.1055/a-2122-4080 UR - https://m2.mtmt.hu/api/publication/34060723 ID - 34060723 AB - Oxindole is a widely used scaffold in drug discovery, which can be found in several marketed drugs, among them the widely used sunitinib or ziprasidone. Thus, the derivatization of oxindole is of considerable current interest. The extreme reaction conditions (high temperature, high pressure), described in the literature for the batchwise regioselective multistep 3-alkylation of oxindole with alcohols in the presence of Raney nickel, motivated us to develop a robust, time- and cost-efficient continuous-flow variant for this reaction. In addition, the continuous-flow technology was also extended to the reductive 3-alkylation of oxindole with aldehydes. The elaborated methodology allows the safe use of Raney nickel, this cheap and widely applied, albeit pyrophoric catalyst. Under the optimized reaction conditions, 10 oxindole derivatives were synthesized ranging from simple 3-alkyl to 3-aralkyl derivatives including two (trifluoromethyl)benzyl congeners. The technology is considerably robust and the catalyst showed a long-term usability. The model reaction between oxindole and acetaldehyde could be run for 19 h uninterruptedly, rendering possible the efficient ethylation of about 20 g oxindole utilizing only approximately 800 mg of Raney nickel. LA - English DB - MTMT ER - TY - JOUR AU - Orsy, György AU - Shahmohammadi, Sayeh AU - Forró, Enikő TI - A Sustainable Green Enzymatic Method for Amide Bond Formation JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 15 PG - 11 SN - 1431-5157 DO - 10.3390/molecules28155706 UR - https://m2.mtmt.hu/api/publication/34082152 ID - 34082152 AB - A sustainable enzymatic strategy for the preparation of amides by using Candida antarctica lipase B as the biocatalyst and cyclopentyl methyl ether as a green and safe solvent was devised. The method is simple and efficient and it produces amides with excellent conversions and yields without the need for intensive purification steps. The scope of the reaction was extended to the preparation of 28 diverse amides using four different free carboxylic acids and seven primary and secondary amines, including cyclic amines. This enzymatic methodology has the potential to become a green and industrially reliable process for direct amide synthesis. LA - English DB - MTMT ER - TY - JOUR AU - Orsy, György AU - Forró, Enikő TI - Lipase-Catalyzed Strategies for the Preparation of Enantiomeric THIQ and THβC Derivatives: Green Aspects JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 17 PG - 14 SN - 1431-5157 DO - 10.3390/molecules28176362 UR - https://m2.mtmt.hu/api/publication/34123133 ID - 34123133 N1 - Export Date: 20 September 2023 CODEN: MOLEF Correspondence Address: Forró, E.; Institute of Pharmaceutical Chemistry, Eötvös u. 6, Hungary; email: forro.eniko@szte.hu Funding details: Hungarian Scientific Research Fund, OTKA, K-138871 Funding details: Emberi Eroforrások Minisztériuma, EMMI, TKP-2021-EGA-32 Funding text 1: The authors’ thanks are due to the Hungarian Research Foundation (OTKA No. K-138871) and the Ministry of Human Capacities, Hungary, grant TKP-2021-EGA-32. AB - This report reviews the most important lipase-catalyzed strategies for the preparation of pharmaceutically and chemically important tetrahydroisoquinoline and tetrahydro-β-carboline enantiomers through O-acylation of the primary hydroxy group, N-acylation of the secondary amino group, and COOEt hydrolysis of the corresponding racemic compounds with simple molecular structure, which have been reported during the last decade. A brief introduction describes the importance and synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline derivatives, and it formulates the objectives of this compilation. The strategies are presented in chronological order, classified according to function of the reaction type, as kinetic and dynamic kinetic resolutions, in the main text. These reactions result in the desired products with excellent ee values. The pharmacological importance of the products together with their synthesis is given in the main text. The enzymatic hydrolysis of the hydrochloride salts as racemates of the starting amino carboxylic esters furnished the desired enantiomeric amino carboxylic acids quantitatively. The enzymatic reactions, performed in tBuOMe or H2O as usable solvents, and the transformations carried out in a continuous-flow system, indicate clear advantages, including atom economy, reproducibility, safer solvents, short reaction time, rapid heating and compression vs. shaker reactions. These features are highlighted in the main text. LA - English DB - MTMT ER - TY - JOUR AU - Németh, András György AU - Szabó, Renáta AU - Orsy, György AU - Mándity, István AU - Keserű, György Miklós AU - Ábrányi-Balogh, Péter TI - Continuous-Flow Synthesis of Thioureas, Enabled by Aqueous Polysulfide Solution JF - MOLECULES J2 - MOLECULES VL - 26 PY - 2021 IS - 2 PG - 9 SN - 1431-5157 DO - 10.3390/molecules26020303 UR - https://m2.mtmt.hu/api/publication/31816807 ID - 31816807 LA - English DB - MTMT ER - TY - THES AU - Orsy, György TI - Continuous-flow methodologies for deuteration of haloarenes, N-acetyaltion and amide formation reactions [Folyamatos áramú szintéziseljárások haloarének deuterálásra, N-acetilációra és amid képződési reakcióra] PB - Szegedi Tudományegyetem (SZTE) PY - 2021 SP - 55 DO - 10.14232/phd.10728 UR - https://m2.mtmt.hu/api/publication/32852862 ID - 32852862 LA - English DB - MTMT ER - TY - JOUR AU - Orsy, György AU - Fülöp, Ferenc AU - Mándity, István TI - N-Acetylation of Amines in Continuous-Flow with Acetonitrile-No Need for Hazardous and Toxic Carboxylic Acid Derivatives JF - MOLECULES J2 - MOLECULES VL - 25 PY - 2020 IS - 8 PG - 12 SN - 1431-5157 DO - 10.3390/molecules25081985 UR - https://m2.mtmt.hu/api/publication/31346572 ID - 31346572 AB - A continuous-flow acetylation reaction was developed, applying cheap and safe reagent, acetonitrile as acetylation agent and alumina as catalyst. The method developed utilizes milder reagent than those used conventionally. The reaction was tested on various aromatic and aliphatic amines with good conversion. The catalyst showed excellent reusability and a scale-up was also carried out. Furthermore, a drug substance (paracetamol) was also synthesized with good conversion and yield. LA - English DB - MTMT ER - TY - JOUR AU - Orsy, György AU - Fülöp, Ferenc AU - Mándity, István TI - Direct amide formation in a continuous-flow system mediated by carbon disulfide JF - CATALYSIS SCIENCE & TECHNOLOGY J2 - CATAL SCIENCE & TECHNOLOGY VL - 23 PY - 2020 IS - 10 SP - 7814 EP - 7818 PG - 5 SN - 2044-4753 DO - 10.1039/d0cy01603a UR - https://m2.mtmt.hu/api/publication/31665283 ID - 31665283 LA - English DB - MTMT ER - TY - JOUR AU - Orsy, György AU - Fülöp, Ferenc AU - Mándity, István TI - Continuous-flow catalytic deuterodehalogenation carried out in propylene carbonate JF - GREEN CHEMISTRY J2 - GREEN CHEM VL - 21 PY - 2019 IS - 5 SP - 956 EP - 961 PG - 6 SN - 1463-9262 DO - 10.1039/c8gc03192d UR - https://m2.mtmt.hu/api/publication/30638150 ID - 30638150 AB - A selective continuous-flow (CF) deuterodehalogenation approach is described performed in propylene carbonate, which is considered as one of the greenest solvents. Various CF technologies are known for hydrodehalogenation reactions; however, they are not directly transferable for deuteration transformations. A novel spherical activated carbon-supported palladium catalyst has been found to be useful for the catalytic deuterodehalogenation of haloarenes. After careful reaction parameter optimization, complete conversion was achieved for bromine-and chlorine-substituted haloarenes. Nonetheless, no deuterium exchange was observed for the fluorine substituent, while iodine-substituted compounds poisoned the catalyst. Importantly, deuterated compounds were obtained with a rate of 3 mg min-1 and the catalyst showed reasonable reusability. Moreover, benzylic amides were also deuterated without any debenzylation side-reaction. LA - English DB - MTMT ER - TY - JOUR AU - Kiss, Loránd AU - Forró, Enikő AU - Orsy, György AU - Ábrahámi, Renáta AU - Fülöp, Ferenc TI - Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives JF - MOLECULES J2 - MOLECULES VL - 20 PY - 2015 IS - 12 SP - 21094 EP - 21102 PG - 9 SN - 1431-5157 DO - 10.3390/molecules201219749 UR - https://m2.mtmt.hu/api/publication/2985673 ID - 2985673 LA - English DB - MTMT ER -