TY - JOUR AU - Piros, László AU - Krajsovszky, Gábor AU - Bogdán, Dóra AU - Gáti, T. AU - Szabó, P. AU - Horváth, Péter AU - Mándity, István TI - Energy-Efficient Synthesis of Haloquinazolines and Their Suzuki Cross-Coupling Reactions in Propylene Carbonate JF - CHEMISTRYSELECT J2 - CHEMISTRYSELECT VL - 9 PY - 2024 IS - 10 PG - 6 SN - 2365-6549 DO - 10.1002/slct.202304969 UR - https://m2.mtmt.hu/api/publication/34744209 ID - 34744209 AB - Comparative synthesis of some new quinazoline derivatives via tetrakis(triphenylphosphine)palladium(0) catalysed Suzuki-Miyaura cross-coupling reaction in “green” propylene carbonate (PC) and dimethoxyethane. Three haloquinazolines were synthesised for Suzuki-cross-coupling from 5-bromoanthranilic acid. Sufficient and easy method for the elimination of PC is developed, thus the optimization of the synthesis of some quinazoline derivatives was carried out. Reactions with 2-chloro-6-bromo-3-phenylquinazolin-4(3H)-one proceeded faster and with a higher yield in PC than in dimethoxyethane, thus for some reactants PC is a good choice for greener synthesis. Practical considerations for using PC include shorter reaction times, improved yields, and the elimination of unnecessary solvent distillation, leading to significant energy savings. This facilitates the execution of energy-efficient reactions in a notably environmentally friendly solvent. In contrast to DME, the use of PC does not necessitate special pre-treatments. Moreover, less PC is required due to its high boiling point and low volatility. Considering these properties, coupled with the consistent need for chromatographic purification, the use of PC in the Suzuki-Miyaura cross-coupling reaction emerges as a superior and greener alternative compared to DME. © 2024 The Authors. ChemistrySelect published by Wiley-VCH GmbH. LA - English DB - MTMT ER - TY - JOUR AU - Faragó, Tünde AU - Remete, Attila Márió AU - Szatmári, István AU - Ambrus, Rita AU - Palkó, Márta TI - The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives JF - RSC ADVANCES J2 - RSC ADV VL - 13 PY - 2023 IS - 28 SP - 19356 EP - 19365 PG - 10 SN - 2046-2069 DO - 10.1039/D3RA03528J UR - https://m2.mtmt.hu/api/publication/34035454 ID - 34035454 N1 - Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged, H-6720, Hungary Stereochemistry Research Group, Eötvös Loránd Research Network, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Institute of Pharmaceutical Technology and Regulatory Affairs Faculty of Pharmacy, University of Szeged, Eötvös utca 6, Szeged, H-6720, Hungary Export Date: 24 July 2023 CODEN: RSCAC Correspondence Address: Palkó, M.; Institute of Pharmaceutical Chemistry, Eötvös utca 6, Hungary; email: palko.marta@szte.hu Funding details: ÚNKP-22-3-SZTE-150 Funding details: Hungarian Scientific Research Fund, OTKA, K-138871 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA, TKP2021-EGA-32 Funding details: Innovációs és Technológiai Minisztérium 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. T. F: was supported by the ÚNKP-22-3-SZTE-150 New National Excellence Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund. The high-resolution mass spectrometric (HRMS) analysis was performed by Robert Berkecz. Project no. TKP2021-EGA-32 has been implemented with the support provided by the Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund, financed under the TKP2021-EGA funding scheme. AB - This work involves the synthesis and subsequent development of a number of novel organocatalysts generated from β-amino acids bearing diendo and diexo norbornene skeletons to improve their catalytic characteristics. LA - English DB - MTMT ER - TY - JOUR AU - Alfano, Antonella Ilenia AU - Lange, Heiko AU - Brindisi, Margherita TI - Amide bonds meet flow chemistry: a journey into methodologies and sustainable evolution JF - CHEMSUSCHEM J2 - CHEMSUSCHEM VL - 15 PY - 2022 IS - 6 SN - 1864-5631 DO - 10.1002/cssc.202102708 UR - https://m2.mtmt.hu/api/publication/32600867 ID - 32600867 N1 - SPOTS-Lab – Sustainable Pharmaceutical and Organic Technology and Synthesis Laboratory, University of Naples ‘Federico II', Department of Pharmacy, Via Domenico Montesano 49, Naples, 80131, Italy University of Milano-Bicocca Department of Earth and Environmental Sciences, Piazza della Scienza 1, Milan, 20126, Italy Export Date: 20 February 2022 CODEN: CHEMI Correspondence Address: Brindisi, M.; SPOTS-Lab – Sustainable Pharmaceutical and Organic Technology and Synthesis Laboratory, Via Domenico Montesano 49, Italy; email: margherita.brindisi@unina.it Correspondence Address: Lange, H.; University of Milano-Bicocca Department of Earth and Environmental Sciences, Piazza della Scienza 1, Italy; email: heiko.lange@unimib.it LA - English DB - MTMT ER - TY - JOUR AU - Masui, H. AU - Fuse, S. TI - Recent Advances in the Solid- and Solution-Phase Synthesis of Peptides and Proteins Using Microflow Technology JF - ORGANIC PROCESS RESEARCH & DEVELOPMENT J2 - ORG PROCESS RES DEV VL - 26 PY - 2022 IS - 6 SP - 1751 EP - 1765 PG - 15 SN - 1083-6160 DO - 10.1021/acs.oprd.2c00074 UR - https://m2.mtmt.hu/api/publication/33003341 ID - 33003341 N1 - Export Date: 19 July 2022 CODEN: OPRDF Correspondence Address: Fuse, S.; Department of Basic Medicinal Sciences, Furo-cho, Chikusa-ku, Japan; email: fuse@ps.nagoya-u.ac.jp LA - English DB - MTMT ER - TY - JOUR AU - Hernandez, Dacil AU - Carro, Carmen AU - Boto, Alicia TI - "Doubly Customizable" Unit for the Generation of Structural Diversity: From Pure Enantiomeric Amines to Peptide Derivatives JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 86 PY - 2021 IS - 3 SP - 2796 EP - 2809 PG - 14 SN - 0022-3263 DO - 10.1021/acs.joc.0c02751 UR - https://m2.mtmt.hu/api/publication/32056320 ID - 32056320 N1 - Funding Agency and Grant Number: project APOGEO (Cooperation Program INTERREG-MAC 2014-2020); European Funds for Regional Development-FEDEREuropean Commission; Plan Estatal I+D-RETOS (MINECO-MCIU)-European Social Funds (ESF) [SAF-2013-48399-R]; MINECO/Min. Science and Innovation [DI-14-06736]; BIOSIGMA SL; Cabildo de Tenerife, Program TF INNOVA 2016-21 (MEDI Fund); Cabildo de Tenerife, Program TF INNOVA 2016-21 (FDCAN Fund) Funding text: This work was partly financed by project APOGEO (Cooperation Program INTERREG-MAC 2014-2020, with European Funds for Regional Development-FEDER) and by project SAF-2013-48399-R, Plan Estatal I+D-RETOS (MINECO-MCIU)-European Social Funds (ESF). D.H. also acknowledges her current contract (TRANSALUDAGRO) financed by Cabildo de Tenerife, Program TF INNOVA 2016-21 (with MEDI & FDCAN Funds). C.C. was granted a contract from the Doctorados Industriales Programme (DI-14-06736) by MINECO/Min. Science and Innovation, cofinanced by BIOSIGMA SL. C.C. carried out her work as a Ph.D. student of the program "Quimica e Ingenieria Quimica" of the University of La Laguna (ULL). ISSN:0022-3263 AB - Readily available, low-cost 4R-hydroxy-L-proline (Hyp) is introduced as a "doubly customizable" unit for the generation of libraries of structurally diverse compounds. Hyp can be cleaved at two points, followed by the introduction of new functionalities. In the first cycle, the removal and replacement of the carboxylic group are carried out, followed (second cycle) by the scission of the 4,5-position and manipulation of the resulting chains. In this way, three new chains are generated and can be transformed independently to afford a diversity of products with tailored substituents, such as beta-amino aldehydes, diamines, beta-amino acid derivatives, including N-alkylated ones, or modified peptides. Many of these products are high-profit compounds but, in spite of their commercial value, are still scarce. Moreover, the process takes place with stereochemical control, and either pure R or S isomers can be obtained with small variations of the synthetic route. LA - English DB - MTMT ER - TY - JOUR AU - Ludmerczki, Róbert AU - Malfatti, Luca AU - Stagi, Luigi AU - Meloni, Manuela AU - Carbonaro, Carlo Maria AU - Casula, Maria Francesca AU - Bogdán, Dóra AU - Mura, Stefania AU - Mándity, István AU - Innocenzi, Plinio TI - Polymerization‐Driven Photoluminescence in Alkanolamine‐Based C‐Dots JF - CHEMISTRY-A EUROPEAN JOURNAL J2 - CHEM-EUR J VL - 27 PY - 2021 IS - 7 SP - 2543 EP - 2550 PG - 8 SN - 0947-6539 DO - 10.1002/chem.202004465 UR - https://m2.mtmt.hu/api/publication/31831955 ID - 31831955 N1 - Funding Agency and Grant Number: Italian Ministry of Education, University and Research (MIUR)Ministry of Education, Universities and Research (MIUR) [2017W75RAE]; Programma Operativo Nazionale (PON) Ricerca e Innovazione 2014-2020-Linea 1 Funding text: The Italian Ministry of Education, University and Research (MIUR) is acknowledged for funding through the project PRIN 2017 no. 2017W75RAE. LS gratefully acknowledges the financial support from Programma Operativo Nazionale (PON) Ricerca e Innovazione 2014-2020-Linea 1. The authors kindly acknowledge Dr. A. Ardu and CeSAR (Centro Servizi Ricerca d'Ateneo) core facility at the University of Cagliari for access to Jeol JEM 1400 Plus and JEM 2010 microscopes. Department of Chemistry and Pharmacy, Laboratory of Materials Science and Nanotechnology, CR-INSTM, University of Sassari, Via Vienna 2, Sassari, 07100, Italy Department of Physics, University of Cagliari, sp 8, km 0.700, Monserrato, 09042, Italy DIMCM–Department of Mechanical, Chemical, and Materials Engineering, INSTM, University of Cagliari, Via Marengo 2, Cagliari, 09123, Italy Department of Organic Chemistry, Semmelweis University, Hőgyes Endre St. 7, Budapest, 1092, Hungary MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, Research Center for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok krt. 2, Budapest, 1117, Hungary Export Date: 4 June 2021 CODEN: CEUJE Correspondence Address: Innocenzi, P.; Department of Chemistry and Pharmacy, Via Vienna 2, Italy; email: plinio@uniss.it Department of Chemistry and Pharmacy, Laboratory of Materials Science and Nanotechnology, CR-INSTM, University of Sassari, Via Vienna 2, Sassari, 07100, Italy Department of Physics, University of Cagliari, sp 8, km 0.700, Monserrato, 09042, Italy DIMCM–Department of Mechanical, Chemical, and Materials Engineering, INSTM, University of Cagliari, Via Marengo 2, Cagliari, 09123, Italy Department of Organic Chemistry, Semmelweis University, Hőgyes Endre St. 7, Budapest, 1092, Hungary MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, Research Center for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok krt. 2, Budapest, 1117, Hungary Export Date: 5 June 2021 CODEN: CEUJE Correspondence Address: Innocenzi, P.; Department of Chemistry and Pharmacy, Via Vienna 2, Italy; email: plinio@uniss.it LA - English DB - MTMT ER - TY - JOUR AU - Tarui, Atsushi AU - Ueo, Masakazu AU - Morikawa, Marino AU - Tsuta, Masahiko AU - Iwasaki, Sumika AU - Morishita, Noriko AU - Karuo, Yukiko AU - Sato, Kazuyuki AU - Kawai, Kentaro AU - Omote, Masaaki TI - One-Pot Ring-Opening Peptide Synthesis Using alpha,alpha-Difluoro-beta-Lactams JF - SYNTHESIS-STUTTGART J2 - SYNTHESIS-STUTTGART VL - 52 PY - 2020 IS - 23 SP - 3657 EP - 3666 PG - 10 SN - 0039-7881 DO - 10.1055/s-0040-1707238 UR - https://m2.mtmt.hu/api/publication/31486601 ID - 31486601 N1 - Cited By :2 Export Date: 21 February 2022 CODEN: SYNTB Correspondence Address: Omote, M.; Faculty of Pharmaceutical Sciences, Japan; email: omote@pharm.setsunan.ac.jp Funding details: Japan Society for the Promotion of Science, KAKEN, JP16K18855 Funding text 1: This work was supported by JSPS KAKENHI Grant Number JP16K18855.JapanSocietyforthePomoionofScience(JP16K18855) AB - alpha,alpha-Difluoro-beta-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the alpha,alpha-difluoro-beta-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form beta-amino acid peptides with alpha,alpha-difluoromethylene unit. LA - English DB - MTMT ER - TY - JOUR AU - Zheng, C. AU - Sun, H. AU - Ma, J. AU - Bi, X. AU - Tang, Y. AU - Shan, B. AU - Zheng, Chunying AU - Sun, Haofen AU - Ma, Jiping AU - Bi, Xuejun AU - Tang, Yizhen AU - Shan, Bin TI - The achiral beta-alanine self organizes into supramolecular helical chains in crystallized achiral beta-alaninium inorganic/organic acid compounds JF - JOURNAL OF MOLECULAR STRUCTURE J2 - J MOL STRUCT VL - 1199 PY - 2020 SN - 0022-2860 DO - 10.1016/j.molstruc.2019.126920 UR - https://m2.mtmt.hu/api/publication/31261295 ID - 31261295 N1 - Cited By :2 Export Date: 26 March 2020 CODEN: JMOSB Correspondence Address: Zheng, C.; School of Environmental and Municipal Engineering, Qingdao University of TechnologyChina; email: 3120110530@bit.edu.cn AB - Helical structures play essential roles in biological systems and the potential physical and chemical properties. The single-stranded and double-stranded supramolecular helical chains are found in six achiral beta-alanine-inorganic-acid (beta-AIA) compounds and one achiral beta-alanine-organic-acid (beta-AOA) compound. The supramolecular helical models of those beta-alanine-acid compounds are classified into four types. And, the law of supramolecular assembly of helical chains in beta-alanine-acid compounds is also summarized. (C) 2019 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Zheng, C. AU - Liu, C. AU - Zhang, X. TI - The self-assembly of supramolecular helical chains in crystallized compounds of methionine with inorganic/organic acids JF - JOURNAL OF MOLECULAR STRUCTURE J2 - J MOL STRUCT VL - 1207 PY - 2020 SN - 0022-2860 DO - 10.1016/j.molstruc.2020.127847 UR - https://m2.mtmt.hu/api/publication/31261293 ID - 31261293 N1 - School of Environmental and Municipal Engineering, Qingdao University of Technology, Qingdao, 266033, China College of Civil Engineering, Qingdao University of Technology, Qingdao, 266033, China Export Date: 26 March 2020 CODEN: JMOSB Correspondence Address: Zheng, C.; School of Environmental and Municipal Engineering, Qingdao University of TechnologyChina; email: 3120110530@bit.edu.cn LA - English DB - MTMT ER - TY - JOUR AU - Zheng, C. AU - Bi, X. AU - Ma, J. AU - Zhao, Y. AU - Gu, C. TI - The self organizing of supramolecular helical chains in crystallized eighteen compounds of L-alanine with inorganic/organic acids JF - JOURNAL OF MOLECULAR STRUCTURE J2 - J MOL STRUCT VL - 1202 PY - 2020 SN - 0022-2860 DO - 10.1016/j.molstruc.2019.127382 UR - https://m2.mtmt.hu/api/publication/31261294 ID - 31261294 N1 - Cited By :1 Export Date: 26 March 2020 CODEN: JMOSB Correspondence Address: Gu, C.; School of Environmental and Municipal Engineering, Qingdao University of TechnologyChina; email: guchuantao@163.com LA - English DB - MTMT ER - TY - JOUR AU - Baykov, Sergey AU - Tarasenko, Marina AU - Zelenkov, Lev E. AU - Kasatkina, Svetlana AU - Savko, Polina AU - Shetnev, Anton TI - Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY J2 - EUR J ORG CHEM VL - 2019 PY - 2019 IS - 33 SP - 5685 EP - 5693 PG - 9 SN - 1434-193X DO - 10.1002/ejoc.201900843 UR - https://m2.mtmt.hu/api/publication/30840823 ID - 30840823 N1 - Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Pr, Peterhof, Saint Petersburg, 198504, Russian Federation Yaroslavl State Technical University, 88 Moscowsky Pr, Yaroslavl, 150023, Russian Federation Perm State University, ul. Bukireva 15, Perm, 614990, Russian Federation Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl, 150000, Russian Federation Cited By :6 Export Date: 21 February 2022 CODEN: EJOCF Correspondence Address: Baykov, S.; Institute of Chemistry, 26 Universitetsky Pr, Peterhof, Russian Federation; email: sergei.v.baikov@yandex.ru Funding details: Russian Foundation for Basic Research, РФФИ, 18-33-01108 Funding details: Saint Petersburg State University, SPbU Funding text 1: This work was financially supported by the Russian Foundation for Basic Research (RFBR) grant No. 18-33-01108. LEZ is grateful to Saint Petersburg State University for a postdoctoral grant. Physicochemical studies were performed at the Magnetic Resonance Research Centre, Center for X-ray Diffraction Studies, Chemical Analysis, and Materials Research Centre (all belong to Saint Petersburg State University). LA - English DB - MTMT ER -