An efficient synthesis of 2,3,4-trisubstituted quinolines through alkynylation-cyclization at ambient temperature

Journal of Heterocyclic Chemistry

Volumn 48, Issue 6, 2011, Pages 1414-1418

  Patil, Dipti R ^a   Salunkhe, Sonali M ^a   Deshmukh, Madhukar B ^a   Anbhule, Prashant V ^a  

^a SHIVAJI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; AMPHOLYTE; QUINOLINE DERIVATIVE;

ALKYNYLATION; ARTICLE; CYCLIZATION; ENVIRONMENTAL TEMPERATURE; SYNTHESIS;

EID: 81855218593     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.715     Document Type: Article

References (48)

1. Beagley, P.; Blackie, M. A. L.; Chibale, K.; Clarkson, C.; Meijboom, R.; Moss, J. R.; Smith, P.; Su, H., Dalton Trans 2003, 15, 3046.
2. Sawada, Y.; Kayakiri, H.; Abe, Y.; Mizutani, T.; Inamura, N.; Asano, M.; Hatori, C.; Aramori, I.; Oku, T.; Tanaka, H., J Med Chem 2004, 47, 2853.
3. Ma, Z.; Hano, Y.; Nomura, T.; Chen, Y., Bioorg Med Chem Lett 2004, 14, 1193.
4. Denton, T. T.; Zhang, X.; Cashman, J. R., J Med Chem 2005, 48, 224.
5. Fokialakis, N.; Magiatis, P.; Chinou, L.; Mitaku, S.; Tillequin, F. M., Chem Pharm Bull 2002, 50, 413.
6. Fossa, P.; Mosti, L.; Menozzi, G.; Marzano, C.; Baccichetti, F.; Bordin, F., Bioorg Med Chem 2002, 10, 743.
7. (a), Ryckebusch, A.; Derprez-Poulain, R.; Maes, L.; Debreu-Fontaine, M. A.; Mouray, E.; Grellier, P.; Sergheraert, C., J Med Chem 2003, 46, 542
8. (b), Morgan, L. R.; Jursic, B. S.; Hooper, C. L.; Neumann, D. M.; Thangaraj, K.; Leblanc, B., Bioorg Med Chem Lett 2002, 12, 3407.
9. Borella, C.; Foley, K.; Sun, L.; Chim-Manamada, D. U.; Li, H.; Xia, Z.; Vo, N.; Bohnert, G.; Chen, S.; Wu, Y., PCT Int Appl WO 2006065842, 2006.
10. Jenekhe, S. A.; Lu, L.; Alam, M. M., Macromolecules 2001, 34, 7315.
11. (a), Jones, G., In Comprehensive Heterocyclic Chemistry II, 5, Katritzky, A. R.; Rees, C W., Ed.; Pergamon Press: New York, 1996, 167
12. (b), Cho, C. S.; Oh, B. H.; Kim, T. J.; Shim, S. C., Chem Commun 2000, 1885
13. (c), Jiang, B.; Si, Y. G. J., Org Chem 2002, 67, 9449
14. (d), Skraup, H., Ber Dtsch Chem Ges 1880, 13, 2086
15. (e), Friedlander, P., Ber Dtsch Chem Ges 1882, 15, 2572
16. (f), Mansake, R. H.; Kulka, M., Org React 1953, 7, 59
17. (g), Linderman, R. J.; Kirollos, K. S., Tetrahedron Lett 1990, 31, 2689
18. (h), Theoclitou, M. E.; Robinson, L. A., Tetrahedron Lett 2002, 43, 3907.
19. Hoemann, M. Z.; Kumaravel, G.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R., Bioorg Med Chem Lett 2000, 10, 2675.
20. Lekhok, C. K.; Prajapati, D.; Boruah, R. C., Synlett 2008, 5, 655.
21. (a), Taylor, E. C.; Heindel N. D., J Org Chem 1967, 32, 1666
22. (b), James, D. S.; Fanta, P. E., J Org Chem 1962. 37, 3346
23. (c), Hendrickson, J. B., Rees, R.; Templeton, J. F., J Am Chem Soc 1964, 36, 107
24. (d), Erickson, E. H.; Lappi, L. R., J Med Chem 1978, 21, 984.
25. (a), Johnson, A. W.; Tebby, J. C., J Chem Soc 1961, 2126
26. (b), Tebby, J. C.; Wilson, I. F.; Griffiths, D. V., J Chem Soc Perkin Trans 1979, 1, 2133
27. (c), Butterfield, P. J.; Tebby, J. C.; Griffiths, D. V., J Chem Soc Perkin Trans 1979, 1, 1189
28. (d), Shaw, M. A.; Tebby, J. C.; Ward, R. S.; Williams, D. H., J Chem Soc 1968, 2795.
29. (a), Diels, O.; Alder, K., Liebigs Ann Chem 1932, 16, 498
30. (b), Acheson, R. M., Adv Heterocycl Chem 1963, 1, 125
31. (c), Acheson, R. M.; Plunkett, A. O., J Chem Soc (London) 1964, 2676.
32. Winterfeldt, E., Chem Ber 1965, 98, 1518.
33. Winterfeldt, E.; Schumann, D.; Dillinger, H., J Chem Ber 1969, 102, 1656.
34. (a), Dillinger, H. J.; Fengler, G.; Schumann, D.; Winterfeldt, E., Tetrahedron 1974, 30, 2553
35. (b), Dillinger, H. J.; Fengler, G.; Schumann, D.; Winterfeldt, E., Tetrahedron 1974, 30, 2561
36. (c), Junjappa, H.; Saxena, M. K.; Ramaiah, D.; Loharay, B. B.; Rath, N. P.; George. M. V., J Org Chem 1998, 63, 9801
37. (d), Takizawa, T.; Obata, N.; Suzuki, Y.; Yanagida, T., Tetrahedron Lett 1969, 10, 3407
38. (e), Suzuki, Y.; Obata, N.; Takizawa. T., Tetrahedron Lett 1970, 11, 2667
39. (f), Oakes, T. R.; David, H. G.; Nagel, F. J., J Am Chem Soc 1969, 91, 4761
40. (g), Oakes, T. R.; D. J. Donovan, J Org Chem 1973, 38, 1319
41. (h), Johnson, F. A.; Gulbenkian, A. H.; Naustavicus, W., J Chem Soc Chem Commun 1970, 608
42. (i), Krebs, A.; Guntner, A.; Versteylen, S.; Schulz, S., Tetrahedron Lett 1984, 25, 2333.
43. Nair, V.; Vinod, A. U.; Abhilash, N.; Menon, R. S.; Santhi, V.; Varma, R. L.; Viji, S.; Mathew, S.; Srinivas, R., Tetrahedron 2003, 59, 10279.
44. Nair, V.; Vinod, A. U.; Rajesh, C., J Org Chem 2001, 66, 4429.
45. (a), Deshmukh, M. B.; Salunkhe, S. M.; Patil, D. R.; Anbhule, P. V., Eur J Med Chem 2009, 44, 2651
46. (b), Deshmukh, M. B.; Anbhule, P. V.; Jadhav, S. D.; Mali, A. R.; Jagtap, S. S.; Deshmukh, S. A., Indian J Chem 2007, 42B, 1445
47. (c), Deshmukh M. B.; Anbhule, P. V.; Jadhav, S. D.; Jagtap, S. S.; Patil, D. R.; Salunkhe, S. M.; Sankpal, S. A., Indian J Chem 2008, 47B, 792.
48. Nair, V.; Vinod, A. U.; Sreekanth, A. R., Org Lett 2001, 3, 3495.