Synthesis of novel 2-(2,2,2-trifluoro-1-aryl-ethylidene)cyclohexane-1,3-dione: Scaffolds for reagent-based diversity-oriented synthesis

References

• (a) Galloway, W. R. J. D.; Osodrp-Llobet, A. D. A. Nat. Commun. 2010, 1, 1.
   PubMed Web of Science ®Google Scholar
  (b) Schreiber, S. L. Science 2000, 287, 1964–1969. DOI: 10.1126/science.287.5460.1964.
   PubMed Web of Science ®Google Scholar
• (a) O’Connor, C. J.; Beckmann, H. S. G.; Spring, D. R. Chem. Soc. Rev. 2012, 41, 4444. DOI: 10.1039/c2cs35023h.
   PubMed Web of Science ®Google Scholar
  (b) Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2017, 139, 5627–5639. DOI: 10.1021/jacs.6b13340.
   PubMed Web of Science ®Google Scholar
  (c) Kim, H.; Tung, T. T.; Park, S. B. Org. Lett. 2013, 15, 5814–5817. DOI: 10.1021/ol402872b.
   PubMed Web of Science ®Google Scholar
  (d) Bandyopadhyay, A.; Mitra, P.; Chattopadhyay, S. K. Synthesis 2013, 4. 0536.
   Google Scholar
  (e) Wu, Q.; Ma, C.; Du, X.-H.; Chen, Y.; Cai, P.-J. Synthesis 2016, 4. 595.
   Google Scholar
• Kim, H.; Bang, K.-T.; Choi, I.; Lee, J.-K.; Choi, T.-L. J. Am. Chem. Soc. 2016, 138, 8612–8622. DOI: 10.1021/jacs.6b04695.
   PubMed Web of Science ®Google Scholar
• Cheng, C.; Gao, N.; Yu, C.; Wang, Z.; Wang, J.; Hao, E.; Wei, Y.; Mu, X.; Tian, Y.; Ran, C.; et al. Org. Lett. 2015, 17, 278–281. DOI: 10.1021/ol503379c.
   PubMed Web of Science ®Google Scholar
• Vendrell, M.; Lee, J.-S.; Chang, Y.-T. Curr. Opin. Chem. Biol. 2010, 14, 383–389. DOI: 10.1016/j.cbpa.2010.02.020.
   PubMed Web of Science ®Google Scholar
• (a) Theodoridis, G. Fluorine-Containing Agrochemicals: An Overview of Recent Developments. In Advances in Fluorine Science, 1st ed.; Tressaud, A., Ed.; Elsevier: Amsterdam, The Netherlands, 2006; Vol. 2, p 122.
   Google Scholar
  (b) Wang, J.; Sánchez-Roselló, M.; Acena, J. L.; Pozo, C. D.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432–2506. DOI: 10.1021/cr4002879.
   PubMed Web of Science ®Google Scholar
  (c) Mei, H.; Han, J.; Fustero, S.; Medio-Simon, M.; Sedgwick, D. M.; Santi, C.; Ruzziconi, R.; Soloshonok, V. A. Chemistry 2019, 25, 11797–11819. DOI: 10.1002/chem.201901840.
   PubMed Web of Science ®Google Scholar
• (a) Mandal, S.; Mandal, S.; Ghosh, S. K.; Ghosh, A.; Saha, R.; Banerjee, S.; Saha, B. Synth. Commun. 2016, 46, 1327–1342. DOI: 10.1080/00397911.2016.1206938.
   Web of Science ®Google Scholar
  (b) Khare, R.; Pandey, J.; Smriti, S.; Ruchi, R. Orient. J. Chem. 2019, 35, 423–429. DOI: 10.13005/ojc/350154.
   Web of Science ®Google Scholar
• (a) Sokolov, V. B.; Aksinenko, A. Y. Russ. J. Gen. Chem. 2014, 84, 1243–1245. DOI: 10.1134/S1070363214060310.
   Web of Science ®Google Scholar
  (b) Kanwar, A.; Eduful, B. J.; Barbeto, L.; Carletti Bonomo, P.; Lemus, A.; Vesely, B. A.; Mutka, T. S.; Azhari, A.; Kyle, D. E.; Leahy, J. W. ACS Med. Chem. Lett. 2017, 8, 797–801. DOI: 10.1021/acsmedchemlett.7b00039.
   PubMed Web of Science ®Google Scholar
  (c) Ahluwalia, V. K.; Rao, J. S. Ind. J. Chem. Section B. 1989, 28B, 81.
   Google Scholar
• (a) Jakhar, A.; Nazish, M.; Gupta, N.; Khan, N.-O. H.; Kureshy, R. I. Chemistry Select 2018, 3, 4838–4843. DOI: 10.1002/slct.201800113.
   Google Scholar
  (b) Jakhar, A.; Amamudin, A.; Sekhar, N.; Gupta, N.; Khan, N.-O. H.; Kureshy, R. I. Chemistry Select 2017, 2, 11346–11351. DOI: 10.1002/slct.201702330.
   Google Scholar
  (c) Tang, l-W.; Li, C.; Zhao, B.-J.; Lan, L.; Zhang, M.; Zhou, Z.-M. Tetrahedron 2017, 73, 923–930. DOI: 10.1016/j.tet.2017.01.001.
   Web of Science ®Google Scholar
• (a) Calabrese, C.; Maris, A.; Evangelisti, L.; Favero, L. B.; Melandri, S.; Caminati, W. J. Phys. Chem. A 2013, 117, 13712–13718. DOI: 10.1021/jp4078097.
   PubMed Web of Science ®Google Scholar
  (b) Alagona, G.; Ghio, C. Int. J. Quantum Chem. 2008, 108, 1840–1855. DOI: 10.1002/qua.21613.
   Web of Science ®Google Scholar
  (c) Sekhar, B. C. J. Heterocyclic Chem. 2004, 41, 807–855. DOI: 10.1002/jhet.5570410601.
   Web of Science ®Google Scholar
  (d) Ribeiro Da Silva, M. A. V.; Ferrao, M. L. C. C. H.; Monte, M. J. S.; Jiye, F. J. Phys. Chem. 1993, 97, 243.
   Web of Science ®Google Scholar
  (e) Manson, M. V. Synthesis of 2-Alkylidene-1,3-Cyclohexanediones. Master’s Dissertations, The College of William and Mary in Virginia, 1984.
   Google Scholar
• Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 1st ed.; Wiley-VCH: Weinheim, Germany, 2005; p 389.
   Google Scholar
• (a) Krygowski, T. M.; Szatyłowicz, H.; Zachara, J. E. J. Org. Chem. 2005, 70, 8859–8865. DOI: 10.1021/jo051354h.
   PubMed Web of Science ®Google Scholar
  (b) Aggarwal, V. K.; Emme, I.; Fulfor, S. Y. J. Org. Chem. 2003, 68, 692–700. DOI: 10.1021/jo026671s.
   PubMed Web of Science ®Google Scholar
  (c) Riddick, J. A.; Bunger, W. B.; Sakano, T. K. Techniques of Chemistry. Organic Solvents. Physical Properties and Methods of Purification, 4th ed. John Wiley and Sons: New York, NY, 1985; Vol. II, p 638.
   Google Scholar
  (d) Hall, H. K. Jr. J. Am. Chem. Soc. 1957, 79, 5441–5444. DOI: 10.1021/ja01577a029.
   Web of Science ®Google Scholar
  (e) Kaupmees, K.; Trummal, A.; Leito, I. Croat. Chem. Acta 2014, 87, 385–395. DOI: 10.5562/cca2472.
   Web of Science ®Google Scholar
• Manabu, A.; Tomohis, U.; Yuji, M.; Tomohiro, M.; Kazutaka, M. PCT Int. Appl. Patent WO2009001942, 2008.
   Google Scholar
• Mishima, M.; Tsuno, Y.; Fujio, M. Chem. Lett. 1990, 19, 2281–2284. DOI: 10.1246/cl.1990.2281.
   Google Scholar
• Values reported from SciFinder,Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02(1994-2019 ACD/Labs).
   Google Scholar
• Anton, A.; Elena, R.; Virgil, B. J. Braz. Chem. Soc. 2010, 3, 489.
   Google Scholar
• Buchanan, G. S.; Cole, K. P.; Tang, Y.; Hsung, R. P. J. Org. Chem. 2011, 76, 7027–7039. DOI: 10.1021/jo200936r.
   PubMed Web of Science ®Google Scholar
• The NMR and MS data for the intermediate 3a and 3c are included in supporting documents.
   Google Scholar