Regioselective synthesis of highly functionalized 3-spiropyrrolidine/ pyrrolizidine oxindoles and acenaphthenones via one-pot four-component [3+2] cycloaddition

Synthesis

Volumn , Issue 11, 2010, Pages 1793-1803

  Zhao, Kai ^a   Zhu, Song Lei ^a   Shi, Da Qing ^a   Xu, Xiao Ping ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Indole containing heterocycles; Multicomponent 3+2 cycloaddition; One pot synthesis; Spirooxindoles

Indexed keywords

FUNCTIONALIZED; HETEROCYCLES; HIGH YIELD; MULTICOMPONENT [3+2] CYCLOADDITION; MULTICOMPONENTS; ONE POT; ONE-POT SYNTHESIS; OXINDOLES; REGIOSELECTIVE SYNTHESIS;

ALDEHYDES; AMINO ACIDS; ORGANIC ACIDS;

SYNTHESIS (CHEMICAL);

3 SPIROPYRROLIDINE ACENAPHTHENONE DERIVATIVE; 3 SPIROPYRROLIDINE OXINDOLE DERIVATIVE; 3 SPIROPYRROLIZIDINE OXINDOLE DERIVATIVE; OXINDOLE; OXINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; REACTION OPTIMIZATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 77952753499     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218731     Document Type: Article

References (62)

1. Nair V, Rajesh C, Vinod A U., Bindu S, Sreekanth A R., Mathen J S., Balagopal L, Acc. Chem. Res. 2003 36 899
2. Armstrong R W., Combs A P., Tempest P A., Brown S D., Keating T A., Acc. Chem. Res. 1996 29 123
3. Tietze L F., Modi A, Med. Res. Rev. 2000 20 304
4. Domling A, Ugi I, Angew. Chem. Int. Ed. 2000 39 3168
5. Weber L, Curr. Med. Chem. 2002 9 2085
6. Orru R V. A., deGreef M, Synthesis 2003 1471
7. Domling A, Chem. Rev. 2006 106 17
8. Feliu L, Vera-Luque P, Albericio F, lvarez M, J. Comb. Chem. 2007 9 521
9. Karthikeyan K, Perumal P T., Etti S, Shanmugam G, Tetrahedron 2007 63 10581
10. Zhu J, Eur. J. Org. Chem. 2003 1133
11. Litvinov Y M., Mortikov V Y., Shestopalov A M., J. Comb. Chem. 2008 10 741
12. Mohammadi A A., Dabiri M, Qaraat H, Tetrahedron 2009 65 3804
13. Devi I, Kumar B S. D., Bhuyan P J., Tetrahedron Lett. 2003 44 8307
14. da Silva J F. M., Garden S J., Pinto A C., J. Braz. Chem. Soc. 2001 12 273
15. Monlineux R J., In Alkaloids: Chemical and Biological Perspective Pelletier S W. Wiley New York 1987 Chap. 1
16. Galliford C V., Scheidt K V., Angew. Chem. Int. Ed. 2007 46 8748
17. Shanmugam P, Viswambharan B, Selvakumar K, Madhavan S, Tetrahedron Lett. 2008 49 2611
18. Pajouhesh H, Parsons R, Popp F D., J. Pharm. Sci. 1983 72 318
19. Popp F D., J. Heterocycl. Chem. 1984 21 1367
20. Dandia A, Singh R, Khaturia S, Merienne C, Morgant G, Loupy A, Bioorg. Med. Chem. 2006 14 2409
21. Chene P, Nat. Rev. Cancer 2003 3 102
22. Ding K, Lu Y, Nikolovska-Coleska Z, Qiu S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller P P., Tomita Y, Parrish D A., Deschamps J R., Wang S, [nl]J. Am. Chem. Soc. 2005 127 10130
23. , Marti C, Carreira E M., Eur. J. Org. Chem. 2003 2209
24. Toyota M, Ihara M, Nat. Prod. Rep. 1998 15 327
25. Lin H, Danishefsky S J., Angew. Chem. Int. Ed. 2003 42 36
26. Lo M M.-C, Neumann C S., Nagayama S, Perlstein E O., Schreiber S L., J. Am. Chem. Soc. 2004 126 16077
27. Dounary A B., Hatanaka K, Kodanko J J., Oestreich M, Pfeifer L A., Weiss M M., J. Am. Chem. Soc. 2003 125 6261; and references therein
28. Skiles J W., McNeil D, Tetrahedron Lett. 1990 31 7277
29. 1,3-Dipolar Cycloaddition Chemistry Padwa A Wiley-Interscience New York 1984
30. Dondas H A., Fishwick C W. G., Grigg R, Kilner C, Tetrahedron 2004 60 3473
31. Boruah M, Konwar D, Sharma S D., Tetrahedron Lett. 2007 48 4535
32. Kawashima K, Kakehi A, Noguchi M, Tetrahedron 2007 63 1630
33. Watson A A., Fleet G W. J., Asano N, Molyneux R J., Nash R J., Phytochemistry 2001 56 265
34. OHagan D, Nat. Prod. Rep. 1997 637
35. Horri S, Fukase H, Matsuo T, Kameda Y, Asano N, Matsui K, J. Med. Chem. 1986 29 1038
36. Spearman M A., Jamieson J C., Wright J A., Exp. Cell Res. 1987 168 116
37. Tsukamoto K, Uno A, Shimada S, Imokaw G, Clin. Res. 1989 37A 722
38. Karpas A, Fleet G W. J., Dwek R A., Petursson S, Mamgoong S K., Ramsden N G., Jacob G S., Rademacher T W., Proc. Natl. Acad. Sci. U.S.A. 1988 85 9229
39. Shanmugam P, Viswambharan B, Madhavan S, Org. Lett. 2007 9 4095
40. Kathiravan S, Raghunathan R, Tetrahedron Lett. 2009 50 6116
41. Shanmugam P, Vaithiyanathan V, Tetrahedron 2008 64 3322
42. SureshBabu A R., Raghunathan R, Tetrahedron Lett. 2008 49 4487
43. Fokas D, Ryan W J., Casebier D S., Coffen D L., Tetrahedron Lett. 1998 39 2235
44. El-Ahl, Abdel-Aziz S, Heteroat. Chem. 2002 13 324
45. Sundberg R J., The Chemistry of Indoles Academic Press New York 1996
46. Shanthi G, Perumal P T., Tetrahedron Lett. 2008 49 7139
47. Casapullo A, Bifulco G, Bruno I, Riccio R, J. Nat. Prod. 2000 63 447
48. Bao B, Sun Q, Yao X, Hong J, Lee C O., Sim C J., Im K S., Jung J H., J. Nat. Prod. 2005 68 711
49. Skibo E B., Xing C, Dorr R T., J. Med. Chem. 2001 44 3545
50. Gupta L, Talwar A, Palne N S., Gupta S, Chauhan P M. S., Bioorg. Med. Chem. Lett. 2007 17 4075
51. Kaniwa K, Arai M A., Li X, Ishibashi M, Bioorg. Med. Chem. Lett. 2007 17 4254
52. Sridhar G, Gunasundari T, Raghunathan R, Tetrahedron Lett. 2007 48 319
53. Periyasami G, Raghunathan R, Surendiran G, Mathivanan N, Bioorg. Med. Chem. Lett. 2008 18 2342
54. Kumar R R., Perumal S, Senthilkumar P, Yogeeswari P, Sriram D, Tetrahedron 2008 64 2962
55. Zhu S.-L, Ji S.-J, Zhang Y, Tetrahedron 2007 49 1777
56. Zhu S.-L, Ji S.-J, Zhao K, Zhang Y, Lett. Org. Chem. 2008 5 319
57. Zhu S.-L, Zhao K, Su X.-M, Ji S.-J, Synth. Commun. 2009 39 1355
58. Zhu S.-L, Ji S.-J, Su X.-M, Sun C, Liu Y, Tetrahedron Lett. 2008 49 1777
59. Zhu S.-L, Ji S.-J, Zhao K, Liu Y, Tetrahedron Lett. 2008 49 2578
60. Zhao K, Xu X.-P, Zhu S.-L, Shi D.-Q, Zhang Y, Ji S.-J, Synthesis 2009 2697
61. For a detailed discussions on the mechanism of azomethine ylide formation by the decarboxylative route, see:, Ardill H, Dorrity M J. R., Grigg R, Leon-Ling M S., Malone J F., Sridharan V, Thainpatanagul S, Tetrahedron 1990 46 6433
62. Ardill H, Xavier L R., Grigg R, Montgomery J, Sridharan V, Surendrakumar S, Tetrahedron 1990 46 6449