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Intermolecular cyclocondensation of arylchloropyruvates in the synthesis of 2,3-dihydrofuran-3,5-dicarboxylic acid derivatives

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Abstract

Methyl arylchloropyruvates undergo intermolecular self-condensation in the presence of a catalytic amount of a base under high-temperature conditions (~250°C) with the formation of 3,4-diaryl-2-oxo-2,3-dihydrofuran-3,5-dicarboxylic acid derivatives.

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References

  1. X. Wu, H. Chen, Tetrahedron, 2008, 64, 10331

    Article  CAS  Google Scholar 

  2. T. Ok, H. Lee, J. Org. Chem., 2009, 72, 7390

    Article  Google Scholar 

  3. V. V. Shchepin, A. E. Korzun, N. V. Bronnikova, Russ. J. Org. Chem. (Engl. Transl.), 2004, 40, 999 [Zh. Org. Khim., 2004, 40, 1040]

    CAS  Google Scholar 

  4. T. Hiroki, U. Yasuhiro, M. Takefumi, J. Org. Chem., 1995, 60, 5628

    Article  Google Scholar 

  5. P. L. Creger, J. Org. Chem., 1972, 37, 1907

    Article  CAS  Google Scholar 

  6. K. Mori, Tetrahedron, 1983, 39, 3107

    Article  CAS  Google Scholar 

  7. L. J. Theodore, W. L. Nelson, J. Org. Chem., 1987, 52, 1309.

    Article  CAS  Google Scholar 

  8. H. R. Rang, M. M. Dale, J. M. Ritter, P. Moore, In Pharmacology, Ed. L. Hunter, 5th ed., London, Churchill Livingstone, 2003, p 144.

  9. C. Kaiser, L. Noronha-Blob, J. Med. Chem. 1992, 35, 4415.

    Article  CAS  Google Scholar 

  10. M. I. Konaklieva, B. J. Plotkin, Mini-Rev. Med. Chem., 2005, 5, 73.

    Article  CAS  Google Scholar 

  11. F. Dickens, H. E. H. Jones, Brit. J. Cancer, 1963, 17, 100

    Article  CAS  Google Scholar 

  12. F. Dickens, H. E. H. Jones, Brit. J. Cancer, 1965, 19, 392

    Article  CAS  Google Scholar 

  13. F. Dickens, H. E. H. Jones, H. B. Waynforth, Brit. J. Cancer, 1966, 20, 134.

    Article  CAS  Google Scholar 

  14. S. M. Kupchan, R. W. Britto, M. F. Ziegler, C. J. Gilmore, R. J. Restivo, R. F. Bryan, J. Am. Chem. Soc., 1973, 95, 1335

    Article  CAS  Google Scholar 

  15. S. M. Kupchan, M. Maruyama, R. J. Hemingway, J. C. Hemingway, S. Shibuya, T. Fujita, J. Org. Chem., 1973, 38, 2189.

    Article  CAS  Google Scholar 

  16. J. Estephane, A. Doutheau, Bioorg. Med. Chem. Lett., 2008, 18, 4321

    Article  CAS  Google Scholar 

  17. G. D. Geske, H. E. Blackwell, Bioorg. Med. Chem. Lett., 2008, 18, 5978.

    Article  CAS  Google Scholar 

  18. M. Ito, T. Ikariya, Org. Lett., 2007, 9, 1821

    Article  CAS  Google Scholar 

  19. E. Abraham, A. D. Smith, Tetrahedron, 2007, 63, 5855

    Article  CAS  Google Scholar 

  20. M. M. Kayser, C. M. Clouthier, J. Org. Chem. 2006, 71, 8424

    Article  CAS  Google Scholar 

  21. D. Hoppe, Angew. Chem., Int. Ed. Engl., 1984, 23, 932.

    Article  Google Scholar 

  22. V. A. Mamedov, E. A. Berdnikov, S. Tsuboi, H. Hamamoto, T. Komiyama, E. A. Gorbunova, A. T. Gubaidullin, I. A. Litvinov, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 1455 [Izv. Akad. Nauk, Ser. Khim., 2006, 1402].

    Article  CAS  Google Scholar 

  23. V. A. Mamedov, I. A. Nuretdinov, Bull. Russ. Acad. Sci., Div. Chem. Sci. (Engl. Transl.), 1992, 41, 1690 [Izv. Akad. Nauk, Ser. Khim., 1992, 2159].

    Article  Google Scholar 

  24. L. A. Kazitsyna, N. B. Kupletskaya, Primenenie UF-, IK- i YaMR-spektroskopii v organicheskoi khimii [Application of UV, IR, and NMR-spectroscopy in Organic Chemistry], Vysshaya shkola, Moscow, 1971, 264 pp. (in Russian).

    Google Scholar 

  25. V. A. Mamedov, I.A. Litvinov, I. A. Nuretdinov, Bull. Russ. Acad. Sci., Div. Chem. Sci. (Engl. Transl.), 1990, 39, 2226 [Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 2454].

    Article  Google Scholar 

  26. V. A. Mamedov, I. A. Litvinov, A. T. Kh. Lenstra, Yu. Ya. Efremov, V. A. Naumov, I. A. Nuretdinov, Bull. Russ. Acad. Sci., Div. Chem. Sci. (Engl. Transl.), 1991, 40, 1267 [Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1427].

    Article  Google Scholar 

  27. V. A. Mamedov, A. T. Gubaidullin, I. A. Litvinov, S. Tsuboi, Heterocycles, 2000, 52, 1385.

    Article  CAS  Google Scholar 

  28. V. A. Mamedov, S. Tsuboi, L. V. Mustakimova, H. Hamamoto, A. T. Gubaidullin, I. A. Litvinov, Ya. A. Levin, Chem. Heterocycl. Compd. (Engl. Transl.), 2000, 36, 911 [Khim. Geterotsikl. Soedin.,, 2000, 8, 1042].

    Article  CAS  Google Scholar 

  29. J. R. Cannon, V. A. Patrick, C. L. Raston, A. H. White, Aust. J. Chem., 1978, 31, 6, 1265–1283.

    Article  CAS  Google Scholar 

  30. W. Adam, K. Peters, M. Sauter, Synthesis, 1994, 1, 111.

    Article  Google Scholar 

  31. W. Adam, L. Hadjiarapoglou, Th. Mosandl, C. R. Saha-Möller, D. Wild, Angew. Chem., 1991, 103, 187.

    Article  CAS  Google Scholar 

  32. Y. Kawase, S. Yamaguchi, H. Ochiai, H. Horita, Bull. Chem. Soc. Jpn, 1974, 47, 2660.

    Article  CAS  Google Scholar 

  33. N. Brine, A. Foucaud, Bull. Soc. Chim. Fr., 1993, 130, 620.

    CAS  Google Scholar 

  34. G. Rio, B. Serkiz, Bull. Soc. Chim. Fr., 1976, 1491.

    Google Scholar 

  35. G. M. Sheldrick, SADABS. Bruker AXS Inc., Madison, USA, 1997.

    Google Scholar 

  36. A. Altomare, G. Cascarano, C. Giacovazzo, D. Viterbo, Acta Crystallogr. Sect. A, 1991, 47, 744.

    Article  Google Scholar 

  37. G. M. Sheldrick, SHELXL-97. Program-s for Crystal Structure Analysis (Release 97-2). University of Göttingen, Göttingen, 1997, Vols 1, 2.

    Google Scholar 

  38. L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837.

    Article  CAS  Google Scholar 

  39. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program-(Version 7.31A), Bruker Advanced X-ray Solutions, Bruker AXS Inc., Madison, Wisconsin, USA, 2006.

    Google Scholar 

  40. T. Hirayama, M. Okaniwa, T. Imada, A. Ohashi, M. Ohori, K. Iwai, K. Mori, T. Kawamoto, A. Yokota, T. Tanaka, T. Ishikawa, Bioorg. Med. Chem., 2013, 21, 5488.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. A. Mamedov, E. A. Khafizova, A. I. Zamaletdinova, A. B. Dobrynin, I. A. Litvinov & O. G. Sinyashin

  2. Kazan National Research Technological University, 68 ul. K. Marksa, 420015, Kazan, Russian Federation

    V. A. Mamedov, E. A. Khafizova, A. I. Zamaletdinova & O. G. Sinyashin

Authors
  1. V. A. Mamedov
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  2. E. A. Khafizova
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  3. A. I. Zamaletdinova
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  4. A. B. Dobrynin
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  5. I. A. Litvinov
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  6. O. G. Sinyashin
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Correspondence to V. A. Mamedov.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2865—2868, December, 2015.

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Mamedov, V.A., Khafizova, E.A., Zamaletdinova, A.I. et al. Intermolecular cyclocondensation of arylchloropyruvates in the synthesis of 2,3-dihydrofuran-3,5-dicarboxylic acid derivatives. Russ Chem Bull 64, 2865–2868 (2015). https://doi.org/10.1007/s11172-015-1239-1

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  • DOI: https://doi.org/10.1007/s11172-015-1239-1

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