DOI QR코드

DOI QR Code

'One Pot' Synthesis of 2-Amino-3-cyano-4,6-diarylpyridines under Ultrasonic Irradiation and Grindstone Technology

  • Gupta, Ragini (Department of Chemistry, Malaviya National Institute of Technology) ;
  • Jain, Anshu (Department of Chemistry, Malaviya National Institute of Technology) ;
  • Jain, Meenakshi (Department of Chemistry, University of Rajasthan) ;
  • Joshi, Rahul (Department of Chemistry, University of Rajasthan)
  • 투고 : 2010.08.10
  • 심사 : 2010.09.04
  • 발행 : 2010.11.20

초록

A simple facile 'one pot' synthesis of 2-amino-3-cyano-4,6-diarylpyridine derivatives via three component reaction of chalcone, malanonitrile and ammonium acetate under ultrasonic irradiation and grindstone technology. All the synthesized compounds have been characterized on the basis of their elemental analyses and spectral data (IR, $^1H$ NMR, $^{13}C$ NMR and Mass).

키워드

참고문헌

  1. Krohnke, K. Synthesis 1976, 1.
  2. Katritzky, A. R.; Elisseou, E. M.; Patel, R. C.; Plau, B. J. Chem. Soc., Perkin Trans. 1 1982, 125.
  3. Steenwinkel, P.; James, S. L.; Grove, D. M.; Kooijman, H.; Spek, A. L.; Koten, G. V. Organometallics 1997, 16, 513. https://doi.org/10.1021/om960943y
  4. Neve, F.; Campagna, S.; Crispini, A. Inorg. Chem. 1997, 36, 6150. https://doi.org/10.1021/ic9703540
  5. Cave, G. W. V.; Hallett, J.; Errington, W.; Rourke, J. P. Angew. Chem. 1998, 23, 3466
  6. Cave, G. W. V.; Hallett, J.; Errington, W.; Rourke, J. P. Angew. Chem., Int. Ed. 1998, 37, 3270. https://doi.org/10.1002/(SICI)1521-3773(19981217)37:23<3270::AID-ANIE3270>3.0.CO;2-2
  7. Constable, E. C.; Housecroft, C. E.; Neuburger, M.; Phillips, D.; Raithby, P. R.; Schofield, E.; Sparr, E.; Tocher, D. A.; Zehnder, M.; Zimmermann, Y. J. Chem. Soc., Dalton Trans. 2000, 2219.
  8. Cave, G. W. V.; Hardie, M. J.; Roberts, B. A.; Raston, C. L. Eur. J. Org. Chem. 2001, 3227.
  9. Constable, E. C.; Housecroft, C. E.; Neuburger, M.; Schneider, A. G.; Springler, B.; Zehnder, M. Inorg. Chim. Acta 2000, 49, 300.
  10. Li, Y.; Liu, Y.; Bu, W.; Guo, J.; Wang, Y. Chem. Commun. 2000, 1551.
  11. Rice, C. R.; Ward, M. D.; Nazeeruddin, M. K.; Grazel, M. New J. Chem. 2000, 24, 651. https://doi.org/10.1039/b003823g
  12. Cave, G. W. V.; Fanizzi, F. P.; Deeth, R. J.; Errington, W.; Rourke, J. P. Organometallics 2000, 19, 1801.
  13. Konda, S. G.; Khedkar, V. T.; Dawane, B. S. J. Chem. Pharm. Res. 2010, 2, 187.
  14. Temple, C. J.; Rener, G. A.; Waud, W. R.; Noker, P. E. J. Med. Chem. 1992, 35, 3686. https://doi.org/10.1021/jm00098a014
  15. Budgett, C. O.; Woodward, C. F. J. Am. Chem. Soc. 1947, 69, 2907.
  16. Mercier, J.; Gavend, M.; Vanluv, V.; Dessaigne, S. Congr Unionther Int [CR] 1963, 8, 361.
  17. Dorner, G.; Fischer, F. W. Arezenmittel Forch 1961, 11, 110.
  18. Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880. https://doi.org/10.1021/jo00002a077
  19. Boger, D. L.; Kasper, A. M. J. Am. Chem. Soc. 1989, 111, 1517. https://doi.org/10.1021/ja00186a067
  20. Zhang, T. Y.; Stout, J. R.; Keay, J. G.; Seriven, E. F. V.; Toomey, J. E.; Goe, G. L. Tetrahedron 1995, 51, 13177. https://doi.org/10.1016/0040-4020(95)00788-A
  21. Youngdale, G. A. US Pat. 4 288 440, 1980
  22. Youngdale, G. A. Chem. Abstr. 1982, 96, 6596.
  23. Todd, A. H.; UK Pat. 1 203, 149, 1970.
  24. Todd, A. H.; Chem. Abstr. 73, 120509, 1970.
  25. Lohaus, G.; Dittmar, W.; Afric, S. Pat. 6 906, 036, 1968
  26. Lohaus, G.; Dittmar, W.; Afric, S.; Chem. Abstr. 73, 120508, 1970.
  27. Gachet, C.; Cattanea, M.; Ohlmann, P.; Lecchi, B.; Cassel, J.; Mannucci, P.; Cazenave, J. P. Br. J. Haematol. 1995, 91, 434. https://doi.org/10.1111/j.1365-2141.1995.tb05319.x
  28. Wang, H.; Helgeson, R.; Ma, B.; Wudl, F. J. Org. Chem. 2000, 65, 5862. https://doi.org/10.1021/jo0005666
  29. Kanbara, T.; Kushida, T.; Saito, N.; Kuwajima, I.; Kubota, K.; Yamamoto, T. Chem. Lett. 1992, 583.
  30. Meyer, T. J. Acc. Chem. Res. 1989, 22, 163. https://doi.org/10.1021/ar00161a001
  31. Harada, H.; Watanuki, S.; Takuwa, T.; Kawaguchi, K.; Okazaki, T.; Harano, Y.; Saitoh, C. PCT Int. Appl. WO 2002, 006, 237 A1, 2002, 92.
  32. Murata, T.; Shimada, M.; Sakakibara, S.; Yoshino, T.; Kadono, H.; Masuda, T.; Shimazaki, M.; Shintani, T.; Fuchikami, K.; Sakai, K.; Inbe, H.; Takeshita, K.; Niki, T.; Umeda, M.; Bacon, K. B.; Ziegelbauer, K. B.; Lowinger, T. B. Bioorg. Med. Chem. Lett. 2003, 13, 913. https://doi.org/10.1016/S0960-894X(02)01046-6
  33. Shishoo, C. J.; Devani, M. B.; Bhadti, V. S.; Ananthan, S.; Ullas, G. V. Tetrahedron Lett. 1983, 24, 4611. https://doi.org/10.1016/S0040-4039(00)85969-9
  34. Doe, K.; Avasthi, K.; Pratap, R.; Bakuni, D. S.; Joshi, M. N. Indian J. Chem. 1990, 29B, 459.
  35. Bhalerao, U. T.; Krishnaiah, A. Ind. J. Chem. 1995, 34B, 587.
  36. Al-Haiza, M. A.; Mostafa1, M. S.; El-Kady, M. Y. Molecules 2003, 8, 275. https://doi.org/10.3390/80200275
  37. Janis, R. A.; Silver, P. J.; Triggle, D. J. Adv. Drug Res. 1987, 16, 309.
  38. Tyndall, D. V.; Nakib, T. A.; Meegan, M. J. Tetrahedron Lett. 1988, 29, 2703. https://doi.org/10.1016/0040-4039(88)85265-1
  39. Al-Arab, M. M. J. Heterocycl. Chem. 1989, 26, 1665. https://doi.org/10.1002/jhet.5570260629
  40. Cave, G. W. V.; Raston, C. L. J. Chem. Soc., Perkin Trans. 1 2001, 3258.
  41. Luche, J. L. Synthetic Organic Sonochemistry; Plenum Press: New York, 1998.
  42. Li, J. T.; Yang, W. Z.; Wang, S. X.; Li, S. H.; Li, T. S. Ultrason.Sonochem. 2002, 9, 237. https://doi.org/10.1016/S1350-4177(02)00079-2
  43. Pathak, V. N.; Gupta, R.; Varshney, B. Indian J. Chem. B 2008, 47, 434.
  44. Cheng, M. S.; Li, R. S.; Kenyon, G. Chinese Chemical Letters 2000, 11, 851.

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