CAN-catalyzed syntheses of 3,4-dihydroquinoxalin-2-amine derivatives based on isocyanides

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6502-6505

  Li, Jian ^a   Liu, Yuejin ^a   Li, Chunju ^a   Jia, Xueshun ^a  

^a SHANGHAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROQUINOXALIN 2 AMINE DERIVATIVE; AMMONIUM NITRATE; CERIUM; CYANAMIDE; ISOCYANIDE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 77953120594     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.022     Document Type: Article

References (34)

1. (a) For recent reviews on multicomponent reactions, see: Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005;
2. (b) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
3. For reviews on isocyanides based MCRs, see: (a) DÖmling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168;
4. (b) DÖmling, A. Chem. Rev. 2006, 106, 17;
5. (c) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
6. Notable exceptions are the also normally divalent carbenes and carbon monoxide.
7. For some recently reported examples with isocyanide, see: (a) Silva, R. A. D.; Santra, S.; Andreana, P. R. Org. Lett. 2008, 10, 4541;
8. (b) Fujiwara, S.-I.; Asanuma, Y.; Shinike, T.; Kambe, N. J. Org. Chem. 2007, 72, 8087;
9. (c) Shaabani, A.; Rezayan, A. H.; Ghasemi, S.; Sarvary, A. Tetrahedron Lett. 2009, 50, 1456;
10. (d) Haravi, M. M.; Baghernejad, B.; Oskooie, H. A. Tetrahedron Lett. 2009, 50, 767;
11. (e) Shaabani, A.; Maleki, A.; Mofakham, H.; Khavasi, H. R. J. Comb. Chem. 2008, 10, 323.
12. (a) Arthur, G.; Elor, K. B.; Robert, G. S.; Guo, Z. Z.; Richard, J. P.; Stanley, D.; John, R. K.; Sean, T. J. Med. Chem. 2005, 48, 744;
13. (b) Lainne, E. S.; William, J. S.; Robert, C. R. J. Med. Chem. 2002, 45, 5604;
14. (c) Andres, J.; Belen, Z.; Ibnacio, A.; Antonio, M. J. Med. Chem. 2005, 48, 2019.
15. (a) Bailly, C.; Echepare, S.; Gago, F.; Waring, M. Anti-Cancer Drug Des. 1999, 15, 291;
16. (b) Dell, A.; William, D. H.; Morris, H. R.; Smith, G. A.; Feeney, J.; Roberts, J. C. K. J. Am. Chem. Soc. 1975, 97, 2497.
17. Jonathan, L. S.; Hiromitsu, M.; Toshihisa, M.; Vincent, M. L.; Hiroyuki, F. Chem. Commun. 2002, 862.
18. Sascha, O.; Rudiger, F. Synlett 2004, 1509.
19. (a) Kazunobu, T.; Ryusuke, T.; Tomohiro, O.; Shuichi, M. Chem. Commun. 2002, 212;
20. (b) Hegedus, L. S.; Marc, M. G.; Jory, J. W.; Joseph, P. B. J. Org. Chem. 2003, 68, 4179.
21. Peter, P. C.; Gang, Z.; Grace, A. M.; Carlos, H.; Linda, M. G. T. Org. Lett. 2004, 6, 333.
22. For the application of CAN in organic synthesis, see: (a) Nair, V.; Deepthi, A. Chem. Rev. 2007, 107, 1862;
23. (b) Varala, R.; Nuvula, S.; Adapa, S. R. Synlett 2006, 1549;
24. (c) More, S. V.; Sastry, M. N. V.; Yao, C. F. Green Chem. 2006, 8, 91.
25. (a) Li, J.; Li, S. Y.; Jia, X. S. Synlett 2008, 1529;
26. (b) Li, J.; Xu, H.; Zhang, Y. M. Tetrahedron Lett. 2005, 46, 1931;
27. (c) Li, J.; Qian, W. X.; Zhang, Y. M. Tetrahedron 2004, 60, 5793.
28. The significance of the CAN was also verified by the blank experiments. In the absence of CAN, no reaction took place at all.
29. Ceric ammonium nitrate can act as efficient catalyst for the preparation of 1,5-benzodiazepine derivatives with substituted o-phenyleneamines and ketones: Varala, R.; Enugala, R.; Nuvula, S.; Adapa, S. R. Synlett 2006, 1009.
30. 13C NMR, EA, MS and IR spectroscopy.
31. Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron 1997, 53, 59.
32. Sannigrahi, M. Tetrahedron 1999, 55, 9007.
33. Nair, V.; Balagopal, L.; Rajan, R.; Mathew, J. Acc. Chem. Res. 2004, 37, 21.
34. 2: C, 64.53; H, 7.65; N, 17.71. Found: C, 64.40; H, 7.80; N, 17.53.