Copper-free palladium-catalyzed sonogashira coupling-annulation: Efficient one-pot synthesis of functionalized pyrano[4,3-b]quinolines from 2-chloro-3-formylquinolines

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5664-5666

  Chandra, Atish ^a   Singh, Bhawana ^a   Khanna, Ranjana S ^a   Singh, Radhey M ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZED PRODUCTS; FUNCTIONALIZED; ONE POT; ONE-POT SYNTHESIS; REACTION MIXTURE; REACTION TIME; SONOGASHIRA COUPLING;

PALLADIUM;

1 METHOXY 3 PHENYL 1H PYRANO[4,3 B]QUINOLINE; 1 METHOXY 8 METHYL 3 PHENYL 1H PYRANO[4,3 B]QUINOLINE; COPPER; PALLADIUM; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; SONOGASHIRA REACTION;

EID: 68049095153     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900606j     Document Type: Article

References (48)

1. (a) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4680.
2. (b) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198.
3. (c) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
4. (a) Woon, E. C. Y.; Dhami, A.; Mahon, M. F.; Threadgill, M. D. Tetrahedron 2006, 62, 4829-4837.
5. (b) Wang, L.; Wang, S. Tetrahedron Lett. 1998, 39, 7625-7628.
6. (a) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980-988.
7. (b) Zhang, H.; Larock, R. C. J. Org. Chem. 2003, 68, 5132-5138.
8. (a) Terrason, V.; Michaux, J.; Gaucher, A.; Wehbe, J.; Marque, S.; Prim, D.; Campagne, J. M. Eur. J. Org. Chem. 2007, 32, 5332-5335.
9. (b) Reboredo, F. J.; Treus, M.; Estevez, J. C.; Castedo, L.; Estevez, R. J. Synlett 2002, 999-1001.
10. (c) Larock, R. C.; Yum, E. K.; Doty, M. J.; Kelvin, K. C. S. J. Org. Chem. 1995, 60, 3270-3271.
11. (a) Hu, Y.; Yang, Z. Org. Lett. 2001, 3, 1387-1390.
12. (b) Uozumi, Y.; Kato, K.; Hayashi, T. J. Org. Chem. 1998, 63, 5071-5075.
13. (c) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625.
14. (d) Trend, R. M.; Ramtohul,Y. K.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892-2895.
15. (e) Trend, R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778-17788.
16. (f) Muniz, K. Adv. Synth. Catal. 2004, 346, 1425-1428.
17. (a) Larock, R. C.; Wei, L.; Hightower, T. R. Synlett 1998, 522-524.
18. (b) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064.
19. (a) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 4, 553-556.
20. (b) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297-299.
21. (c) Nevado, C.; Echavarren, A. M. Synthesis 2005, 167-182.
22. (d) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690.
23. (e) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662.
24. (a) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans. 1 2002, 622-628.
25. (b) Gamila, M. M.; El-Taeb, Evans, A. B.; Jones, S.; Knight, D. W. Tetrahedron Lett. 2001, 42, 5945-5948.
26. (c) Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron 2001, 57, 2857-2870.
27. (d) Djuardi, E.; McNelis, E. Tetrahedron Lett. 1999, 40, 7193-7196.
28. (a) Venkatraman, S.; Barange,D. K.; Pal, M. Tetrahedron Lett. 2006, 47, 7317-7322.
29. (b) Pal, M.; Venkatraman, S.; Yeleswarapu, K. R. Tetrahedron Lett. 2003, 44, 8221-8225.
30. (c) Venkatraman, S.; Batchu, V. R.; Barange, D. K.; Pal, M. J. Org. Chem. 2005, 70, 4778-4783.
31. (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764-765.
32. (b) Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139-5142.
33. (c) Mondal, S.; Nogami, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2003, 68, 9496-9498.
34. (a) Singh, R. M.; Singh, B.; Chandra, A.; Upadhyay, S. Tetrahedron Lett. 2008, 49, 6423-6425.
35. (b) Singh, R. M.; Singh, M. K.; Chandra, A.; Singh, B. Tetrahedron Lett. 2007, 48, 5987-5990.
36. (c) Singh, R. M.; Chandra, A.; Singh, M. K. Synth. Commun. 2007, 37, 1689-1695.
37. (d) Singh, R. M.; Srivastava, A.; Chandra, A. Indian J. Chem. 2007, 46B, 303-307.
38. (e) Singh, R. M.; Srivastava, A.; Singh, M. K. Indian J. Chem. 2006, 45B, 292-296.
39. (f) Singh, R. M.; Srivastava, A.; Chandra, A. Indian J. Chem. 2005, 44B, 2077-2081.
40. Singh, R. M.; Chandra, A.; Singh, B.; Upadhyay, S. Tetrahedron 2008, 64, 11680-11685.
41. Singh, R. M.; Srivastava, A. Indian J. Chem. 2005, 44B, 1868-1875.
42. (a) Yamada, N.; Kadowaki, S.; Takahashi, K.; Umezu, K. Biochem. Pharmacol. 1992, 44, 1211-1213.
43. (b) Faber, K.; Stueckler, H.; Kappe, T. J. Heterocycl. Chem. 1984, 21, 1177-1181.
44. (c) Johnson, J. V.; Rauckmann, B. S.; Baccanari, D. P.; Roth, B. J. Med. Chem. 1989, 32, 1942-1949.
45. (d) Mohmed, E. A. Chem. Pap. 1994, 48, 261-267;
46. Chem. Abstr. 1995, 123, 9315x
47. Godet, T.; Bosson, J.; Belmont, P. Synlett 2005, 2786-2790.
48. Yue, D.; Ca, N. D.; Larock, R. C. J. Org. Chem. 2006, 71, 3381-3388.