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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 23
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Original Articles

Synthesis of benzylidenecycloalkan-1-ones and 1,5-diketones under Claisen–Schmidt reaction: Influence of the temperature and electronic nature of arylaldehydes

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Pages 2202-2214 | Received 07 Jul 2017, Published online: 09 Nov 2017

References

  • (a)Bansal, R.; Narang, G.; Zimmer, C.; Hartmann, R. W. Med. Chem. Res. 2011, 20, 661–669. (b) Prakasham, A. P.; Saxena, A. K.; Luqman, S.; Chanda, D.; Kaur, T.; Gupta, A.; Yadav, D. K.; Chanotiya, C. S.; Shanker, K.; Khan, F. Bioorg. Med. Chem. 2012, 20, 3049–3057. (c) Huang, L.; Lu, Ch.; Sun, Y.; Mao, F.; Luo, Z.; Su, T.; Jiang, H.; Shan, W.; Li, X. J. Med. Chem. 2012, 55, 8483–8492. (d) Sugimoto, H.; Yamanishi, Y.; Iimura, Y.; Kawakami, Y. Curr. Med. Chem. 2000, 3, 303–339. (e) Leoni, L. M.; Hamel, E.; Genini, D.; Shih, H.; Carrera, C. J.; Cottam, H. B.; Carson, D. A. J. Natl. Cancer Inst. 2000, 92, 217–224.
  • Lévai, A. ARKIVOC 2004, vii, 15–33.
  • Verma, A. K.; Pratap, R. Tetrahedron 2012, 68, 8523–8538.
  • Kinzel, O.; Fattori, D.; Muraglia, E.; Gallinari, P.; Nardi, M. C.; Paolini, C.; Roscilli, G.; Toniatti, C.; Gonzalez Paz, O.; Laufer, R. J. Med. Chem. 2006, 49, 5404–5407.
  • Lozano González, M.; Sánchez-Vergara, M. E.; Álvarez-Bada, J. R.; Chávez-Uribe, M. I.; Toscano, R. A.; Álvarez-Toledano, C. J. Mater. Chem. C 2014, 2, 5607–5614.
  • Ciliberto, G.; De Francesco, R.; Fattori, D.; Gallinari, P.; Kinzel, O. D.; Koch, U.; Muraglia, E.; Toniatti, C. US Patent 20070087346 A1, 2007.
  • Dadiboyena, S. Eur. J. Med. Chem. 2013, 63, 347–377.
  • Lévai, A. J. Heterocycl. Chem. 2004, 41, 299 -310.
  • Furniss, B. S.; Hannaford, A. J.; Smith, P. W.; Tatchell, G. A. R. Vogel’s Textbook of Practical Organic Chemistry, 5th ed.; Wiley: New York, 1989; pp 395–469.
  • Perjési, P.; Nusserb, T.; Tarczayc, G.; Sohár, P. J. Mol. Struct. 1999, 479, 13–19.
  • Mufato, J. D.; Vega, D. R.; Aguirre, J. M.; de la Faba, D. J.; Lantaño, B. J. Mol. Struct. 2011, 987, 119–125.
  • Camps, P.; Domingo, L. R.; Formosa, X.; Galdeano, C.; González, D.; Muñoz-Torrero, D.; Segalés, S.; Font-Bardia, M.; Solans, X. J. Org. Chem. 2006, 71, 3464–3471.
  • (a) Berthelette, C.; McCooye, C.; Leblanc, Y.; Trimble, L. A.; Tsou, N. N. J. Org. Chem. 1997, 62, 4339–4342. (b) Leblanc, Y.; Dufresne, C.; Dhawan, R.; Ollerenshaw, J.; Littke, A.; Trimble, L. A.; Tsou, N. N. Can. J. Chem. 2000, 78, 784–790. (c) Gupta, R.; Jindal, D. P.; Jit, B.; Narang, G.; Palusczak, A.; Hartmann, R. W. Arch. Pharm. Pharm. Med. Chem. 2004, 337, 398–401. (d) Narang, G.; Jindal, D. P.; Jit, B.; Bansal, R.; Potter, B. S.; Palmer, R. A. Helv. Chim. Acta 2006, 89, 258–264.
  • (a) Krohnke, F. Synthesis 1976, 1, 1–24. (b) Kharchenko, V. G.; Markova, L. I.; Fedotova, O. V.; Pchelintseva, N. V. Chem. Heterocycl. Compd. 2003, 39, 1121–1142. (c) Kharchenko, V. G.; Pchelintseva, N. V.; Markova, L. I.; Fedotova, O. V. Chem. Heterocycl. Compd. 2000, 36, 1007–1025. (d) Constable, E. C.; Cargill Thompson, A. M. W. J. Chem. Soc., Dalton Trans. 1992, 20, 2947–2950. (e) Butler, I. R.; Mcdonald, S. J. Polyhedron 1995, 14, 529–539.
  • (a) Parr, R. G.; Yang, W. Rev. Phys. Chem. 1995, 46, 701–728. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648–5652. (c) Geerlings, P.; De Proft, F., Langenaeker, W. Chem. Rev. 2003, 103, 1793–1873.
  • Parr, R. G.; Donnelly, R. A.; Levy, M.; Palke, W. E. J. Chem. Phys. 1978, 68, 3801–3807.
  • Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512–7516.
  • Parr, R. G.; von Szentpaly, L.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922–1924.
  • Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049–4050.
  • Chattaraj, P. K.; Maiti, B.; Sarkar, U. J. Phys. Chem. 2003, 107, 4973–4975.
  • (a) Parthasarathi, R.; Padmanabhan, J.; Elango, M.; Subramanian, V.; Chattaraj, P. K. Chem. Phys. Lett. 2004, 394, 225–230. (b) Roy, R. K. J. Phys. Chem. A 2004, 108, 4934–4939.
  • Meneses, L.; Tiznado, W.; Contreras, R. R.; Fuentealba, P. Chem. Phys. Lett. 2004, 383, 181–187.
  • Kadayat, T. M.; Song, C.; Shin, S.; Magar, T. B. T.; Bist, G.; Shrestha, A.; Thapa, P.; Na, Y.; Kwon, Y.; Lee, E. Bioorg. Med. Chem. 2015, 23, 3499–3512.
  • Kelsey, M. C.; Le, C.; Stambuli, J. P. Chem. Eur. J. 2014, 20, 11336–11339.
  • (a) Pavel, G. V.; Tilichenko, M. N. Zh. Org. Khim 1982, 18(3), 671. (b) Pavel, G. V.; Tilichenko, M. N.; Smelik, L. V. Zh. Org. Khim 1985, 21(4), 882–886.

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