Fe(II)/Et3N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives.

作者: Ekaterina E Galenko , Olesya A Tomashenko , Alexander F Khlebnikov , Mikhail S Novikov , Taras L Panikorovskii

DOI: 10.3762/BJOC.11.189

关键词: CatalysisTautomerOrganic chemistryChemistryBetaineMedicinal chemistryImidazoleYlideCascade reactionCarbeneIsoxazole

摘要: … with N-heterocyclic carbenes 5 and betaine 6 (Scheme 1). Interplay between N-heterocyclic carbenes, heterocyclic betaines and ylides is currently intensively investigated as a …

参考文章(39)
A V Galenko, A F Khlebnikov, M S Novikov, V V Pakalnis, N V Rostovskii, Recent advances in isoxazole chemistry Russian Chemical Reviews. ,vol. 84, pp. 335- 377 ,(2015) , 10.1070/RCR4503
Nazar Pidlypnyi, Fabian Uhrner, Martin Nieger, Martin H. H. Drafz, Eike G. Hübner, Jan C. Namyslo, Andreas Schmidt, N-Heterocyclic Carbene–Betaine Interconversions: Tautomeric Equilibria of Imidazolium-Indolates and Indole-Substituted Imidazol-2-ylidenes European Journal of Organic Chemistry. ,vol. 2013, pp. 7739- 7748 ,(2013) , 10.1002/EJOC.201300728
Terri G. Edwards, Kevin J. Koeller, Urszula Slomczynska, Kam Fok, Michael Helmus, James K. Bashkin, Chris Fisher, HPV episome levels are potently decreased by pyrrole–imidazole polyamides Antiviral Research. ,vol. 91, pp. 177- 186 ,(2011) , 10.1016/J.ANTIVIRAL.2011.05.014
Laure Benhamou, Stéphanie Bastin, Noël Lugan, Guy Lavigne, Vincent César, Metal-assisted conversion of an N-ylide mesomeric betaine into its carbenic tautomer: generation of N-(fluoren-9-yl)imidazol-2-ylidene complexes. Dalton Transactions. ,vol. 43, pp. 4474- 4482 ,(2014) , 10.1039/C3DT53089B
Elke Bergmann-Leitner, Editorial [Hot Topic: Anti-Cancer Drugs Executive Editor: Elke Bergmann-Leitner] Current Pharmaceutical Design. ,vol. 15, pp. 730- 731 ,(2005) , 10.2174/138161208784246207
Raymond D. W. Kemmitt, Simon Mason, John Fawcett, David R. Russell, Synthesis and reactivity of N-acetylamino acidate(2–) and related complexes of platinum(II) Journal of The Chemical Society-dalton Transactions. pp. 1165- 1176 ,(1992) , 10.1039/DT9920001165
Ken-Ichi Shinohara, Toshikazu Bando, Hiroshi Sugiyama, Anticancer activities of alkylating pyrrole-imidazole polyamides with specific sequence recognition. Anti-Cancer Drugs. ,vol. 21, pp. 228- 242 ,(2010) , 10.1097/CAD.0B013E328334D8F9
Michael G. Natchus, Roger G. Bookland, Biswanath De, Neil G. Almstead, Stanislaw Pikul, Michael J. Janusz, Sandra A. Heitmeyer, Erin B. Hookfin, Lily C. Hsieh, Martin E. Dowty, Charles R. Dietsch, Vikram S. Patel, Susan M. Garver, Fei Gu, Matthew E. Pokross, Glen E. Mieling, Timothy R. Baker, David J. Foltz, Sean X. Peng, David M. Bornes, Michael J. Strojnowski, Yetunde O. Taiwo, Development of new hydroxamate matrix metalloproteinase inhibitors derived from functionalized 4-aminoprolines. Journal of Medicinal Chemistry. ,vol. 43, pp. 4948- 4963 ,(2000) , 10.1021/JM000246E
Barbara Forte, Beatrice Malgesini, Claudia Piutti, Francesca Quartieri, Alessandra Scolaro, Gianluca Papeo, A Submarine Journey: The Pyrrole-Imidazole Alkaloids Marine Drugs. ,vol. 7, pp. 705- 753 ,(2009) , 10.3390/MD7040705