Synthesis of annulated heterocyclic systems based on 4-CF3- or 4-CHF2-3-cyano-(1H)-pyridine-2-thiones

详细信息    查看全文

• 作者：L. A. Rodinovskaya (1)
  A. E. Fedorov (1)
  A. M. Shestopalov (1)
  P. A. Belyakov (1)
  K. G. Nikishin (1)
  
• 关键词：Claisen condensation ; 3 ; cyano ; 4 ; difluoromethylpyridine ; 2(1H) ; thione ; trifluoromethyl ; 3 ; cyclopyridine ; 2(1H) ; thione ; domino reactions ; 3 ; aminothieno[2 ; 3 ; b]pyridines ; 1 ; 4 ; diazepinediones ; 4 ; hydroxy ; 1H ; thieno[2 ; 3 ; b ; 4 ; 5 ; b鈥瞉dipyridin ; 2 ; one ; pyrido[3鈥?2鈥?4 ; 5] ; thieno[3 ; 2 ; b] ; 4H ; pyrano[2 ; 3 ; d]pyridine
• 刊名：Russian Chemical Bulletin
• 出版年：2013
• 出版时间：October 2013
• 年：2013
• 卷：62
• 期：10
• 页码：2214-2226
• 全文大小：391 KB
• 参考文献：1. L. A. Rodinovskaya, A. M. Shestopalov, A. V. Gromova, A. A. Shestopalov, / J. Comb. Chem., 2008, 10, 313. CrossRef
  2. N. M. Rateb, / J. Sulfur Chem., 2011, 32, 611. CrossRef
  3. V. O. Iaroshenko, Y. Wang, B. Zhang, D. Volochnyuk, V. Ya. Sosnovskikh, / Synthesis, 2009, 2393.
  4. Ch. Zhao, C. Tovar, X. Yin, Q. Xu, I. T. Todorov, L. T. Vassilev, Li Chen, / Bioorg. Med. Chem. Lett., 2009, 19, 319. CrossRef
  5. C. Reichelt, A. Ludwig, A. Schulze, M. Daghish, S. Leistner, A. Krodel, J. Heinicke, US Pat. Appl. Publ., 2008, US 20080160028 A1 20080703.
  6. N. Choi, J. J. Deadman, W. Issa, E. Jones, PCT Int. Appl. (2007), WO 2007124544 A1 20071108.
  7. S. Li, X. Sun, H. Zhao, Y. Tang, M. Lan, / Bioorg. Med. Chem. Lett., 2012, 22, 4004. CrossRef
  8. Q. Huang, A. Deiters, K. Gumireddy, US Pat. Appl. Publ. 2012, US 20120010177 A1 20120112.
  9. B. E. Sleebs, A. Levit, I. P. Street, H. Falk, T. Hammonds, A. C. Wong, M. D. Charles, M. F. Olson, J. B. Baell, / Med-ChemComm, 2011, 2, 977.
  10. L. D. Walensky, M. L. Stewart, N. Cohen, PCT Int. Appl. (2011), WO 2011094708 A2 20110804.
  11. S. Ryder, PCT Int. Appl. 2010, WO 2010151799 A2 20101229.
  12. J. P. Brincat, E. Carosati, S. Sabatini, G. Manfroni, A. Fravolini, J. L. Raygada, D. Patel, G. W. Kaatz, G. Cruciani, / J. Med. Chem., 2011, 54, 354. CrossRef
  13. C. M. Byrd, D. Dai, R. Jordan, D. E. Hruby, PCT Int. Appl. 2010, WO 2010099166 A1 20100902.
  14. Q. Huang, A. Deiters, K. Gumireddy, US Pat. Appl. Publ. 2010, US 20100196357 A1 2010080511.
  15. A. C. Koong, D. E. Feldman, PCT Int. Appl. 2007, WO 2007101225 A2 20070907.
  16. A. C. Koong, D. E. Feldman, PCT Int. Appl. 2007, WO 2007101224 A2 20070907.
  17. Y. Kawazoe, H. Shimogawa, A. Sato, M. Uesugi, / Angew. Chem., Int. Ed., 2011, 50, 5478. CrossRef
  18. Y. W. Ho, W. H. Yao, / Dyes and Pigments, 2005, 70, 60. CrossRef
  19. L. A. Rodinovskaya, Yu. A. Sharanin, V. P. Litvinova, A. M. Shestopalov, V. K. Promonenkov, V. K. Zolotarev, Yu. A. Mortikov, / J. Org. Chem. USSR ( / Engl. Transl.), 1985, 21, 2230 [ / Zh. Org. Khim., 1985, 21, 2439].
  20. V. P. Kislyi, K. G. Nikishin, E. Y. Kruglova, A. M. Shestopalov, V. V. Semenov, A. A. Gakh, A. C. Buchanan, / Tetrahedron, 1996, 52, 10841. CrossRef
  21. K. G. Nikishin, V. P. Kislyi, V. N. Nesterov, A. M. Shestopalov, Yu. T. Struchkov, V. V. Semenov, / Russ. Chem. Bull. ( / Engl. Transl.), 1998, 47, 465 [ / Izv. Akad. Nauk, Ser. Khim., 1998, 482]. CrossRef
  22. K. G. Nikishin, V. N. Nesterov, V. P. Kislyi, A. M. Shestopalov, V. V. Semenov, / Russ. Chem. Bull. ( / Engl. Transl.), 1998, 47, 679 [ / Izv. Akad. Nauk, Ser. Khim., 1998, 701]. CrossRef
  23. A. M. Shestopalov, V. P. Kislyi, E. Y. Kruglova, K. G. Nikishin, V. V. Semenov, A. C. Buchanan, A. A. Gakh, / J. Comb. Chem., 2000, 2, 24. CrossRef
  24. A. E. Fedorov, A. M. Shestopalov, P. A. Belyakov, / Russ. Chem. Bull. ( / Int. Ed.), 2003, 52, 2063 [ / Izv. Akad. Nauk, Ser. Khim., 2003, 2081]. CrossRef
  25. D. E. Thurston, / Mol. Aspects Anticancer Drug-DNA Interact., 1993, 54.
  26. L. A. Rodinovskaya, A. M. Shestopalov, A. V. Gromova, / Russ. Chem. Bull. ( / Int. Ed.), 2003, 52, 2185 [ / Izv. Akad. Nauk, Ser. Khim., 2003, 2069]. CrossRef
  27. L. Rodinovskaya, A. Shestopalov, A. Gromova, A. Shestopalov, / Synthesis, 2006, 2357.
  28. L. A. Rodinovskaya, A. M. Shestopalov, / Russ. Chem. Bull. ( / Int. Ed.), 2000, 49, 348 [ / Izv. Akad. Nauk, Ser. Khim., 2000, 347]. CrossRef
  29. Y. M. Litvinov, A. M. Shestopalov, / Adv. Heterocycl. Chem., 2011, 103, 175. CrossRef
  30. J. S. Martin, A. R. Quirt, / J. Magn. Reson., 1971, 5, 318.
  
• 作者单位：L. A. Rodinovskaya (1)
  A. E. Fedorov (1)
  A. M. Shestopalov (1)
  P. A. Belyakov (1)
  K. G. Nikishin (1)
  
  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
  
• ISSN：1573-9171

文摘

A simple and convenient preparative method for the synthesis of 3-cyano-4-difluoro- and -trifluoromethylpyridine-2(1H)-thiones was developed. During studies of synthetic potential of these compounds, approaches to the synthesis of a number of annulated heterocyclic systems were suggested.