A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction

Organic Letters

Volumn 5, Issue 4, 2003, Pages 435-438

  Bora, Utpal ^a   Saikia, Anil ^a   Boruah, Romesh C ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM OXIDE; CONICEINE; DENDROPRIMINE; INDAZOLIN 167B; INDOLIZINE DERIVATIVE; SLAFRAMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DRUG SYNTHESIS; MICROWAVE RADIATION;

EID: 0042566349     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020238n     Document Type: Article

References (53)

1. (a) Weber, L.; Illegen, K.; Almstetter, M. Synlett 1999, 366.
2. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
3. Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
4. Strecker, A. Liebigs Ann. Chem. 1850, 75, 27.
5. Robinson, R. J. Chem. Soc. (London) 1917, 111, 876.
6. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 215, 1.
7. (a) Bossio, R.; Marcos, C. F.; Marcaccini, S.; Pepino, R. Tetrahedron Lett. 1997, 38, 2519.
8. (b) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. Synthesis 1993, 783.
9. (c) Kobayashi, K.; Matoba, T.; Susumu, I.; Takashi, M.; Morikawa, O.; Konishi, H. Chem. Lett. 1998, 551.
10. (d) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. J. Chem. Soc., Perkin Trans. 1 1996, 229.
11. (a) Yamada, T.; Omote, Y.; Yamanaka, Y.; Miyazawa, T.; Kuwata, S. Synthesis 1998, 991.
12. (b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842.
13. (c) Groger, H.; Hatam, M.; Martens, J. Tetrahedron 1995, 51, 7173.
14. (d) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127.
15. Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1045.
16. (a) Shestopalov, A. M.; Emeliyanova, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D. H. Org. Lett. 2002, 423.
17. (b) List, B.; Castello, C. Synlett 2001, 1687.
18. (c) Nair, V.; Vinod, A. U.; Rajesh, C. J. Org. Chem. 2001, 66, 4427.
19. (d) Bagley, M. C.; Dale, J. W.; Bower, J. Chem. Commun. 2002, 1682.
20. (e) Kappe, C. O. Tetrahedron 1993, 49, 6973.
21. (f) Cheng, J. F.; Chen, M.; Arrhenius, T.; Nadzen, A. Tetrahedron Lett. 2002, 43, 6293.
22. (g) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485.
23. (h) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147.
24. (i) Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309.
25. (a) Pourashraf, M.; Delair, P.; Rasmussen, M. O.; Greene, A. E. J. Org. Chem. 2000, 65, 6966.
26. (b) Cossy, J.; Willis, C.; Bellosta, V.; Jalmes, L. S. Synthesis 2002, 951.
27. Diederich, M.; Nubbemeyer, U. Synthesis 1999, 286.
28. Chalard, P.; Remuson, R.; Mialhe, Y. G.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661.
29. Park, S. H.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621.
30. (a) Gubin, J.; Lucchetti, J.; Mahaux, J.; Nisato, D.; Rosseels, G.; Clinet, M.; Polster, P.; Chatelain, P. J. Med. Chem. 1992, 35, 981.
31. (b) Gubin, J.; Descamps, M.; Chatelain, P. P.; Nisato, D. European Patent EP, 235, 111, 1988.
32. (c) Okada, S.; Sawada, K.; Kuroda, A.; Watanabe, S.; Tanaka, H. European Patent EP, 519353, 1993; Chem Abstr. 1993, 118, 212886.
33. (a) Katritzky A. R.; Rees, C. W.; Scriven, E. F. V., Eds. In Comprehensive Heterocyclic Chemistry II; Elsevier: Oxford, UK, 1996, Vol. 8, p 237.
34. (b) Bonneau, R.; Romashin, Y. N.; Liu, M. T. H.; MacPherson, S. E. J. Chem. Soc., Chem Commun. 1994, 509.
35. (c) Feng, Z.; Lubell, W. D. J. Org. Chem., 2001, 66, 1181.
36. (d) Bhattacharya, J. G.; Su, T.; Chia, C.; Chen, K. J. Org. Chem. 2001, 66, 426.
37. Guet, C.; Blondeau, D.; Silwa, H. J. Chem. Res. (S) 1982, 245.
38. (a) Dinculescu, A.; Balaban, T. S.; Balaban, A. T. Tertrahedron Lett. 1987, 28, 3145.
39. (b) Zhang, L.; Liang, F.; Sun, L.; Hu, Y.; Hu, H. Synthesis 2000, 1733.
40. Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219.
41. Zhou, J.; Hu, Y.; Hu, H. Synthesis 1999, 166.
42. Tanimori, S.; Fukubayashi, K.; Kirihata, M. Tetrahedron Lett. 2001, 42, 4013.
43. Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765.
44. (a) Varma, R. S. In Microwaves: Theory and Application in Material Processing IV; Clark, D. E., Sutton, W. H., Lewis, D. A., Eds.; American Ceramic Society: Westerville, OH, 1997; p 357.
45. (b) Varma, R. S.; Dahiya, R. Tetrahedron 1998, 54, 6293.
46. (c) Varma, R. S.; Meshram, H. M. Tetrahedron Lett. 1997, 38, 7973.
47. (d) Ranu, B. C.; Hajra, A.; Jana, U. Tetrahedron Lett. 2000, 41, 531.
48. (e) Kabalka, G. W.; Wang, L.; Pagni, R. M. Synlett 2001, 676.
49. (f) Bose, A. K.; Manhas, M. S.; Sharma, A. K.; Banik, B. K. Synthesis 2002, 1578.
50. (a) Sharma, U.; Ahmed, S.; Boruah, R. C. Tetrahedron Lett. 2000, 41, 3493.
51. (b) Sharma, U.; Bora, U.; Boruah, R. C.; Sandhu, J. S. Tetrahedron Lett. 2002, 43, 143.
52. 3: C, 73.71; H, 5.15; N, 4.78. Found: C, 73.53; H, 5.19; N, 4.67.
53. Linn, W. J.; Webster, O. W.; Benson, R. E. J. Am. Chem. Soc. 1965, 87, 3651.