dc.contributor.author | Obijalska, Emilia | |
dc.contributor.author | Kowalski, Marcin K. | |
dc.contributor.author | Mlostoń, Grzegorz | |
dc.contributor.author | Heimgartner, Heinz | |
dc.date.accessioned | 2021-11-19T09:49:13Z | |
dc.date.available | 2021-11-19T09:49:13Z | |
dc.date.issued | 2017 | |
dc.identifier.issn | 1551-7004 | |
dc.identifier.uri | http://hdl.handle.net/11089/39808 | |
dc.description | Dedicated to Prof. Jacek Młochowski on the occasion of his 80th birthday. | pl_PL |
dc.description.abstract | The easily available diethyl ethynylphosphonate reacts with diverse aldonitrones under Kinugasa reaction
conditions at room temperature, providing 3‐phosphonylated β‐lactams in good yields. In all cases, the
reaction led to the trans‐isomer exclusively. The trans‐configuration was assigned based on 1H‐NMR spectroscopic analysis. | pl_PL |
dc.description.sponsorship | Authors acknowledge the National Science Center (PL-Cracow) for financial support (Grant OPUS–7 (UMO–
2014/13/B/ST5/04004)). | pl_PL |
dc.language.iso | en | pl_PL |
dc.publisher | ARKAT USA | pl_PL |
dc.relation.ispartofseries | Arkivoc;2 | |
dc.rights | Uznanie autorstwa 4.0 Międzynarodowe | * |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.subject | β‐Lactams | pl_PL |
dc.subject | Kinugasa reaction | pl_PL |
dc.subject | aldonitrones | pl_PL |
dc.subject | ethynylphosphonate | pl_PL |
dc.subject | cycloaddition reactions | pl_PL |
dc.subject | copper(I) catalysis | pl_PL |
dc.title | Application of diethyl ethynylphosphonate to the synthesis of 3‐phosphonylated β‐lactams via the Kinugasa reaction | pl_PL |
dc.type | Article | pl_PL |
dc.page.number | 59-67 | pl_PL |
dc.contributor.authorAffiliation | Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, PL‐91‐403 Łódź, Poland | pl_PL |
dc.contributor.authorAffiliation | Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, PL‐91‐403 Łódź, Poland | pl_PL |
dc.contributor.authorAffiliation | Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, PL‐91‐403 Łódź, Poland | pl_PL |
dc.contributor.authorAffiliation | Department of Chemistry, University of Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, Switzerland | pl_PL |
dc.identifier.eissn | 1551-7012 | |
dc.references | Part of the planned Ph.D. thesis of M. K. K., University of Łódź. | pl_PL |
dc.references | Arya, N.; Jagdale, A. Y.; Patil, T. A.; Yeramwar, S. S.; Holikatti, S. S.; Dwivedi, J.; Shishoo, C. J.; Jain, K. S. Eur. J. Med. Chem. 2014, 74, 619. http://dx.doi.org/10.1016/j.ejmech.2014.01.002 | pl_PL |
dc.references | Burnett, D. A.; Caplen, M. A. Jr.; Davis, H. R.; Burrier, R. E.; Clader, J. W. J. Med. Chem. 1994, 37, 1733. http://dx.doi.org/10.1021/jm00038a001 | pl_PL |
dc.references | Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123. http://dx.doi.org/10.1016/0968‐0896(95)00101‐L | pl_PL |
dc.references | Sun, L.; Vasilevich, N. I.; Fuselier, J. A.; Hocart, S. J.; Coy, D. H. Bioorg. Med. Chem. Lett. 2004, 14, 2041. http://dx.doi.org/10.1016/j.bmcl.2004.02.050 | pl_PL |
dc.references | Sperka, T.; Pitlik, J.; Bagossia, P.; Tożsera, J. Bioorg. Med. Chem. Lett. 2005, 15, 3086. http://dx.doi.org/10.1016/j.bmcl.2005.04.020 | pl_PL |
dc.references | Elliot, T.S.; Slowey, A.; Ye, Y.; Conway, S. J. Med. Chem. Comm. 2012, 3, 735. http://dx.doi.org/10.1039/c2md20079a | pl_PL |
dc.references | Rye, C.; Baell, J. Curr. Med. Chem. 2005, 12, 3127. http://dx.doi.org/10.2174/092986705774933452 | pl_PL |
dc.references | Van Speybrock, V.; Moonen, K.; Hemelsoet, K.; Stevens, C. V.; Waroquier, M. J. Am. Chem. Soc. 2006, 128, 8468. http://dx.doi.org/10.1021/ja0584119 | pl_PL |
dc.references | Moonen, K.; Stevens, C. V. Synthesis 2005, 3603. http://dx.doi.org/10.1055/s‐2005‐918440 | pl_PL |
dc.references | Shiozaki, M.; Masuko, H. Bull. Chem. Soc. Jpn. 1987, 60, 645. http://dx.doi.org/10.1246/bcsj.60.645 | pl_PL |
dc.references | Piotrowska, D. G.; Bujnowicz, A.; Wróblewski, A. E.; Głowacka, I. E. Synlett 2015, 26, 375. http://dx.doi.org/10.1055/s‐0034‐1379506 | pl_PL |
dc.references | Nahmany, M.; Melman, A. J. Org. Chem. 2006, 71, 5804. http://dx.doi.org/10.1021/jo0607010 | pl_PL |
dc.references | Qi, H.; Li, X.; Xu, J. Org. Biomol. Chem. 2011, 9, 2702. http://dx.doi.org/10.1039/C0OB00783H | pl_PL |
dc.references | Candeias, N. R.; Gois, P. M. P.; Afonso, C. A. M. J. Org. Chem. 2006, 71, 5489. http://dx.doi.org/10.1021/jo060397a | pl_PL |
dc.references | Punda, P.; Makowiec, S. New J. Chem. 2013, 37, 2254. http://dx.doi.org/10.1039/C3NJ00192J | pl_PL |
dc.references | Thiery, E.; You, V.; Mora, A.‐S.; Abarbri, M. Eur. J. Org. Chem. 2016, 529. http://dx.doi.org/10.1002/ejoc.201501266 | pl_PL |
dc.references | Oakdale, J. S.; Sit, R. K.; Fokin, V. V. Chem. Eur. J. 2014, 20, 11101 http://dx.doi.org/10.1002/chem.201402559 | pl_PL |
dc.references | Mukai, S.; Flematti, G. R.; Byrne, L. T.; Besant, P. G.; Attwood, P. V.; Piggott, M. J. Amino Acids 2012, 43, 857. http://dx.doi.org/10.1007/s00726‐011‐1145‐2 | pl_PL |
dc.references | McAllister, T. E.; Nix, M. G.; Webb, M. E. Chem. Commun. 2011, 47, 1297. http://dx.doi.org/10.1039/C0CC04238B | pl_PL |
dc.references | Kowalski, M. K.; Mlostoń, G.; Obijalska, E.; Linden, A.; Heimgartner, H. Tetrahedron 2016, in press. | pl_PL |
dc.references | Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. http://dx.doi.org/10.1021/jo00090a0 | pl_PL |
dc.references | Santoro, S.; Liao, R‐Z.; Marcelli, T.; Hammar, P.; Himo, F. J. Org. Chem. 2015, 80, 2649. http://dx.doi.org.10.1021/jo502838p | pl_PL |
dc.references | For a review on the Kinugasa reaction, see: Stecko, S.; Furman, B.; Chmielewski, M. Tetrahedron 2014, 70, 7817. http://dx.doi.org/10.1016/j.tet.2014.06.024 | pl_PL |
dc.references | Vuilhorgne, M.; Malpart J.; Mutti S.; Mignani S. J. Heterocycl. Chem. 2003, 40, 159. http://dx.doi.org/10.1002/jhet.5570400122 | pl_PL |
dc.references | Richmond, E.; Duguet, N.; Slawin, A. M. Z.; Lébl, T.; Smith A. D. Org. Lett. 2012, 14, 2762. http://dx.doi.org/10.1021/ol300982f | pl_PL |
dc.contributor.authorEmail | gmloston@uni.lodz.pl | pl_PL |
dc.identifier.doi | 10.3998/ark.5550190.p009.660 | |
dc.discipline | nauki chemiczne | pl_PL |