A three-component, intramolecular Ugi reaction toward unique indoloketopiperazines

Tetrahedron Letters

Volumn 53, Issue 26, 2012, Pages 3353-3356

  Ghandi, Mehdi ^a   Zarezadeh, Nahid ^a   Taheri, Abuzar ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

Author keywords

Indoloketopiperazines; Isocyanides; Ugi reactions

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; AMINE; CARBOXYLIC ACID; CYANIDE; FORMIC ACID; INDOLE DERIVATIVE; INDOLOKETOPIPERAZINE DERIVATIVE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; POLYMERIZATION; UGI REACTION;

EID: 84861527059     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.04.090     Document Type: Article

References (48)

1. J. Zhu, and H. Bienamye Multicomponent Reactions 2005 VCH Weinheim
2. C. Simon, T. Constantieux, and J. Rodriguez Eur. J. Org. Chem. 2004 4957 4980
3. M. Murakami Angew. Chem., Int. Ed. 42 2003 718 720
4. A. Jacobi Von Vangelin, H. Neumann, D. Gördes, S. Klaus, D. Strübing, and M. Beller Chem. Eur. J. 9 2003 4286 4294
5. G. Balme, E. Bossharth, and N. Monterio Eur. J. Org. Chem. 2003 4101 4111
6. A. Dömling Chem. Rev. 106 2006 17 89
7. C. Hulme, and V. Gore Curr. Med. Chem. 10 2003 51 80
8. V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, and L. Balagopal Acc. Chem. Res. 36 2003 899 907
9. I. Ugi, B. Verner, and A. Dömling Molecules 8 2003 53 66
10. J. Zhu Eur. J. Org. Chem. 2003 1133 1144
11. R.W. Armstrong, A.P. Combs, P.A. Tempest, A.D. Brown, and A.K. Thomas Acc. Chem. Res. 29 1996 123 131
12. V.G. Nenajdenko, A.L. Reznichenko, and E.S. Balenkova Tetrahedron 63 2007 3031 3041
13. A.P. Ilyin, V.V. Kobak, I.G. Dmitrieva, Y.N. Peregudova, V.A. Kustova, Y.S. Mishunina, S.E. Tkachenko, and A.V. Ivachtchenko Synth. Commun. 36 2006 903 910
14. A.P. Ilyin, A.S. Trifilenkov, D.I. Kovrigin, M.V. Yudin, and A.V. Ivachtchenko Heterocycl. Commun. 12 2006 107 110
15. A.P. Ilyin, V.V. Kobak, I.G. Dmitrieva, N.Y. Peregudova, A.V. Kustova, Y.S. Mishunina, S.E. Tkachenko, and A.V. Ivachtchenko Eur. J. Org. Chem. 2005 4670 4679
16. A.P. Ilyn, A.S. Trifilenkov, S.A. Tsirulnikov, A.D. Kurashvily, and A.V. Ivachtchenko J. Comb. Chem. 7 2005 806 808
17. A.P. Ilyn, J.A. Kuzovkova, V.V. Potapov, A.M. Shkirando, D.A. Kovrigin, S.E. Tkachenko, and A.V. Ivachtchenko Tetrahedron Lett. 46 2005 881 884
18. A.P. Ilyin, J.A. Kuzovkova, A.M. Shkirando, and A.V. Ivachtchenko Heterocycl. Commun. 11 2005 523 526
19. S. Kamijo, and Y. Yamamoto J. Org. Chem. 68 2003 4764 4771
20. Y. Hashimoto, K. Shudo, and T. Okamoto Chem. Pharm. Bull. 32 1984 4300 4308
21. Y. Nakashima, Y. Kawashima, F. Amanuma, K. Sota, A. Tanaka, and T. Kameyama Chem. Pharm. Bull. 32 1984 4271 4280
22. M. Taniguchi, T. Anjiki, M. Nakagawa, and T. Hino Chem. Pharm. Bull. 32 1984 2544 2554
23. E. Yamanaka, M. One, S. Kasamatsu, N. Aimi, and S. Sakai Chem. Pharm. Bull. 32 1984 818 821
24. M. Shimizu, M. Ishikawa, Y. Komoda, T. Nkajima, K. Yamaguchi, and N. Yoneda Chem. Pharm. Bull. 32 1984 463 474
25. T. Ohmoto, and K. Koike Chem. Pharm. Bull. 32 1984 170 173
26. J.E. Saxton Indoles 1983 Wiley-Interscience New York Part 4
27. J.S. Carle, and C. Christophersen J. Org. Chem. 45 1980 1586 1589
28. R.J. Sundberg The Chemistry of Indoles 1970 Academic Press New York p 438
29. N. Sakabe, Y. Sendo, I. Iijima, and Y. Ban Tetrahedron Lett. 30 1969 2527 2530
30. N. Haider, and E. Sotero Chem. Pharm. Bull. 50 2002 1479 1483
31. C. Guillonneare, A. Pierre, Y. Charton, N. Guilbaud, I. Kraus-Berthier, S. Leonce, A. Michel, I. Bisagni, and G. Atassi J. Med. Chem. 42 1999 2191 2203
32. Y. Endo, K. Shudo, K. Faruhata, H. Ogura, S. Sakai, N. Aimi, Y. Hitotsuyonagi, and Y. Koyama Chem. Pharm. Bull. 32 1984 358 361
33. S. Sakai, N. Aimi, K. Yamaguchi, Y. Hitotsuyonagi, C. Watanabe, K. Yokose, Y. Koyama, K. Shudo, and A. Itai Chem. Pharm. Bull. 32 1984 354 357
34. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893 930
35. D.S. Thorpe Pharmacogenomics J. 1 2001 229 233
36. V.I. Ognyanov, C. Balan, A.W. Bannon, Y. Bo, C. Dominguez, C. Fotsch, V.K. Gore, L. Klionsky, V.V. Ma, Y.-X. Qian, R. Tamir, X. Wang, N. Xi, S. Xu, D. Zhu, N.R. Gavva, J.J.S. Treanor, and M.H. Norman J. Med. Chem. 49 2006 3719 3742
37. A. Ryckebusch, M.A. Debreu-Fontaine, E. Mouray, P. Grellier, C. Sergheraert, and P. Melnyk Bioorg. Med. Chem. Lett. 15 2005 297 302
38. K. Ding, J. Chen, M. Ji, X. Wu, J. Varady, C.-Y. Yang, Y. Lu, J.R. Deschamps, B. Levant, and S. Wang J. Med. Chem. 48 2005 3171 3181
39. J. Wiesner, K. Kettler, J. Sakowski, R. Ortmann, A.M. Katzin, E.A. Kimura, K. Silber, G. Klebe, H. Jomaa, and M. Schlitzer Angew. Chem., Int. Ed. 43 2004 251 254
40. M.L. López-Rodríguez, D. Ayala, B. Benhamú, M.J. Morcillo, and A. Viso Curr. Med. Chem. 9 2002 1867 1894
41. M. Bös, F. Jenck, J.L. Moreau, V. Mutel, A.J. Sleight, and U. Widmer Eur. Med. Chem. 32 1997 253 261
42. D.R. Goldberg, Y. Choi, D. Cogan, M. Corson, R. DeLeon, A. Gao, L. Gruenbaum, M.H. Hao, D. Joseph, M.A. Kashem, C. Miller, N. Moss, M.R. Netherton, C.P. Pargellis, J. Pelletier, R. Sellati, D. Skow, C. Torcellini, Y.-C. Tseng, J. Wang, R. Wasti, B. Werneburg, J.P. Wua, and Z. Xiong Bioorg. Med. Chem. Lett. 18 2008 938 941
43. S. Röver, D.R. Adams, A. Bénardeau, J.M. Bentley, M.J. Bickerdike, A. Bourson, I.A. Cliffe, P. Coassolo, J.E.P. Davidson, C.T. Dourish, P. Hebeisen, G.A. Kennett, A.R. Knight, C.S. Malcolm, P. Mattei, A. Misra, J. Mizrahi, M. Muller, R.H.P. Porter, H. Richter, S. Taylor, and S.P. Vickers Bioorg. Med. Chem. Lett. 15 2005 3604 3608
44. Menta, E.; Nicotra, F.; Pescalli, N.; Spinelli, S. WO 01/09136 A1, 2001; Chem. Abstr., 2001, 134, 63063x.
45. M. Ghandi, N. Zarezadeh, and A. Taheri Tetrahedron Lett. 52 2011 1228 1232
46. M. Ghandi, N. Zarezadeh, and A. Taheri Tetrahedron 66 2010 8231 8237
47. M. Ghandi, P. Asgari, A. Taheri, and A. Abbasi Cent. Eur. J. Chem. 8 2010 899 905
48. V.J. Majoand, and P.T. Perumal J. Org. Chem. 61 1996 6523 6525