Domino Knoevenagel condensation/intramolecular aldol cyclization route to diverse indolizines with densely functionalized pyridine units

Journal of Organic Chemistry

Volumn 78, Issue 20, 2013, Pages 10395-10404

  Kim, Myungock ^a   Jung, Youngeun ^a   Kim, Ikyon ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZED PYRIDINES; INDOLIZINES; KNOEVENAGEL CONDENSATION; PYRIDINE RINGS;

KETONES; PYRIDINE;

CYCLIZATION;

2 PYRROLECARBOXALDEHYDE; ALDEHYDE; CARBENE; FUNCTIONAL GROUP; INDOLIZINE DERIVATIVE; PYRIDINE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INTRAMOLECULAR ALDOL CYCLIZATION; KNOEVENAGEL CONDENSATION; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; CYCLIZATION; INDOLIZINES; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM;

EID: 84886393739     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401801j     Document Type: Article

References (55)

1. Knoevenagel, E. Chem. Ber. 1896, 29, 172
2. Knoevenagel, E. Chem. Ber. 1894, 27, 2345
3. Ho, T.-L. Tandem Organic Reactions; John Wiley & Sons: New York, 1992.
4. Tietze, L. F. Chem. Rev. 1996, 96, 115
5. Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602
6. Tietze, L. F.; Brasche, G.; Gericke, K. M., Eds.; Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
7. Pellissier, H. Tetrahedron 2006, 62, 2143
8. Chapman, C. J.; Frost, C. G. Synthesis 2007, 1
9. Pellissier, H. Chem. Rev. 2013, 113, 442
10. Tietze, L. F.; Kettschau, G.; Gewart, J. A.; Schuffenhauer, A. Curr. Org. Chem. 1998, 2, 19
11. Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304
12. Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967
13. Tietze, L. F.; Rackelmann, N. In Multicomponent Reactions; Zhu, J.; Bienayme, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005; p 121.
14. Tratrat, C.; Giorgi-Renault, S.; Husson, H.-P. Org. Lett. 2002, 4, 3187
15. Clarke, P. A.; Martin, W. H. C. Org. Lett. 2002, 4, 4527
16. Sabitha, G.; Reddy, G. S. K. K.; Rajkumar, M.; Yadav, J. S.; Ramakrishna, K. V. S.; Kunwar, A. C. Tetrahedron Lett. 2003, 44, 7455
17. Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F., III J. Org. Chem. 2004, 69, 5838
18. Kumar, A.; Maurya, R. A. Tetrahedron 2007, 63, 1946
19. Ramachary, D. B.; Kishor, M. J. Org. Chem. 2007, 72, 5056
20. Verma, R. K.; Verma, G. K.; Shukla, G.; Nagaraju, A.; Singh, M. S. ACS Comb. Sci. 2012, 14, 224
21. Vilches-Herrera, M.; Knepper, I.; de Souza, N.; Villinger, A.; Sosnovskikh, V. Y.; Iaroshenko, V. O. ACS Comb. Sci. 2012, 14, 434
22. Li, M.; Lv, X.-L.; Wen, L.-R.; Hu, Z.-Q. Org. Lett. 2013, 15, 1262
23. Jeyachandran, V.; Kumar, R. R.; Ali, M. A.; Choon, T. S. Bioorg. Med. Chem. Lett. 2013, 23, 2101
24. Kim, I.; Kim, S. G.; Choi, J.; Lee, G. H. Tetrahedron 2008, 64, 664
25. For a recent review on synthesis of heterocycles by domino Knoevenagel condensation/hetero-Diels-Alder reactions, see: Majumdar, K. C.; Taher, A.; Nandi, R. K. Tetrahedron 2012, 68, 5693
26. Toche, R. B.; Bhavsar, D. C.; Kazi, M. A.; Bagul, S. M.; Jachak, M. N. J. Heterocycl. Chem. 2010, 47, 28
27. Wang, K.; Herdtweck, E.; Dömling, A. ACS Comb. Sci. 2012, 14, 316
28. Shen, Q.; Wang, L.; Yu, J.; Liu, M.; Qiu, J.; Fang, L.; Guo, F.; Tang, J. Synthesis 2012, 44, 389
29. Siddiqui, Z. N. Tetrahedron Lett. 2012, 53, 4974
30. Lee, J. H.; Kim, I. J. Org. Chem. 2013, 78, 1283
31. Kim, I.; Choi, J.; Won, H. K.; Lee, G. H. Tetrahedron Lett. 2007, 48, 6863
32. Kim, I.; Won, H. K.; Choi, J.; Lee, G. H. Tetrahedron 2007, 63, 12954
33. Kim, I.; Kim, S. G.; Kim, J. Y.; Lee, G. H. Tetrahedron Lett. 2007, 48, 8976
34. Choi, J.; Lee, G. H.; Kim, I. Synlett 2008, 1243
35. Kim, I.; Choi, J.; Lee, S.; Lee, G. H. Synlett 2008, 2334
36. Kim, K.; Kim, I. J. Comb. Chem. 2010, 12, 379
37. Kim, I.; Kim, K. Org. Lett. 2010, 12, 2500
38. Cho, H.; Kim, I. Tetrahedron 2012, 68, 5464
39. Jung, Y.; Kim, I. Tetrahedron 2012, 68, 8198
40. Flitsch, W. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, p 443.
41. Singh, G. S.; Mmatli, E. E. Eur. J. Med. Chem. 2011, 46, 5237
42. Waldmann, H.; Eberhardt, L.; Wittstein, K.; Kumar, K. Chem. Commun. 2010, 46, 4622
43. Barluenga, J.; Lonzi, G.; Riesgo, L.; López, L. A.; Tomás, M. J. Am. Chem. Soc. 2010, 132, 13200
44. Ziyaadini, M.; Hazeri, N.; Maghsoodlou, M. T.; Habibi-Khorassani, S. M.; Willis, A. C. Tetrahedron Lett. 2011, 52, 5774
45. Mao, Z.; Li, X.; Lin, X.; Lu, P.; Wang, Y. Tetrahedron 2012, 68, 85
46. Kucukdisli, M.; Opatz, T. Eur. J. Org. Chem. 2012, 4555
47. Delcamp, J. H.; Yella, A.; Holcombe, T. W.; Nazeeruddin, M. K.; Grätzel, M. Angew. Chem., Int. Ed. 2013, 52, 376
48. Khoroshilov, G. E.; Tverdokhleb, N. M.; Brovarets, V.; Babaev, E. V. Tetrahedron 2013, 69, 4353
49. Reports on postfunctionalization of the pyridine ring of indolizine core have been scarce. See: Kuznetsov, A. G.; Bush, A. A.; Rybakov, V. B.; Babaev, E. V. Molecules 2005, 10, 1074
50. Zhu, H.; Stöckigt, J.; Yu, Y.; Zou, H. Org. Lett. 2011, 13, 2792
51. While this manuscript is in preparation, Opatz's report on use of α,β-unsaturated carbonyl compounds as three-carbon units for pyridine ring annulation appeared. See: Kucukdisli, M.; Opatz, T. J. Org. Chem. 2013, 78, 6670
52. Thyrann, T.; Lightner, D. A. Tetrahedron Lett. 1995, 36, 4345
53. Wallace, D. M.; Leung, S. H.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1993, 58, 7245
54. Liang, F.; Hu, J.; Zhang, L.; Hu, Y.; Hu, H. J. Heterocycl. Chem. 2001, 38, 853
55. Ohta, T.; Fukuda, T.; Ishibashi, F.; Iwao, M. J. Org. Chem. 2009, 74, 8143