A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families

Tetrahedron Letters

Volumn 53, Issue 43, 2012, Pages 5787-5790

  De Moliner, Fabio ^a   Hulme, Christopher ^a,b  

^a UNIVERSITY OF ARIZONA   (United States)

^b University of Arizona   (United States)

Author keywords

Heterocycles; Imidazoquinoxalines; Multicomponent reactions; TOSMICs

Indexed keywords

1,2 PHENYLENEDIAMINE; BENZYLGLYOXAMIDE; CYANIDE; ETHYL GLYOXYLATE; GLYOXYLIC ACID DERIVATIVE; IMIDAZOLE; IMIDAZOQUINOXALINE; NUCLEOPHILE; QUINOXALINE DERIVATIVE; TOSYLMETHYLISOCYANIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; DEPROTECTION REACTION; MICROWAVE RADIATION; POLYMERIZATION;

EID: 84866356856     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.072     Document Type: Article

References (49)

1. D. Van Leusen, and A.M. Van Leusen L.E. Overman, Synthetic Uses of Tosylmethyl Isocyanide (TOSMIC) in Organic Reactions 2004 Wiley Hoboken, New Jersey 417 666
2. A.M. Van Leusen, J. Wildeman, and O.H. Oldenziel J. Org. Chem. 42 1977 1153
3. B. Wu, J. Wen, J. Zhang, J. Li, Y.-Z. Xiang, and X.-Q. Yu Synlett 3 2009 500
4. M. Chakrabarty, R. Basak, Y. Harigaya, and H. Takayanagi Tetrahedron 61 2005 1793
5. J.M. Atkins, and E. Vedejs Org. Lett. 7 2005 3351
6. S. Kotha, and V.R. Shah Synthesis 2007 3653
7. J.M. Kelly, and F.J. Leeper Tetrahedron Lett. 53 2012 819
8. F. Qiu, J. Wu, Y. Zhang, M. Hu, and Y. Yu Tetrahedron Lett. 53 2012 446
9. D. Sanchez-Garcia, J.I. Borrell, and S. Nonell Org. Lett. 11 2009 77
10. J. Clayden, R. Turnbull, and I. Pinto Org. Lett. 6 2004 609
11. A. Dömling, B. Beck, E. Herdtweck, W. Antuch, C. Oefner, N. Yehia, and A. Gracia-Marques ARKIVOC 12 2007 99
12. S. Srivastava, W. Wang, A. Czarna, T.A. Holak, and A. Dömling J. Comb. Chem. 11 2009 631
13. C. Garcia-González, E. González-Zamora, R. Satilla, and N. Farfán Synlett 3 2011 308
14. C. Neochoritis, J. Stephanidou-Stephanatou, and C.A. Tsoleridis Synlett 2 2009 302
15. J. Mendiola, A. Baeza, J. Alvarez-Builla, and J.J. Vaquero J. Org. Chem. 69 2003 4974
16. For exhaustive overviews on this topic see: J. Zhu, and H. Bienaymè Multicomponent Reactions Wiley-VCH 2005 Weinheim Germany
17. A. Dömling Chem. Rev. 106 2006 17
18. A. Dömling, W. Wang, and K. Wang Chem. Rev. 112 2012 3083
19. E. Ruijter, R. Scheffelaar, and R.V.A. Orru Angew. Chem., Int. Ed. 50 2011 6234
20. J.D. Sunderhaus, and S.E. Martin Chem. Eur. J. 15 2009 1300
21. C. Hulme, and J. Dietrich Mol. Diversity 13 2009 195
22. For applications of imidazoles in medicinal chemistry see: L. De Luca Curr. Med. Chem. 13 2006 1
23. M. Boiani, and M. Gonzalez Mini.-Rev. Med. Chem. 5 2005 68
24. See for example: W. Antuch, S. Menon, Q.Z. Chen, Y. Lu, S. Sakamuri, B. Beck, V. Schauer-Vukašinović, S. Agarwal, S. Hess, and A. Dömling Bioorg. Med. Chem. Lett. 16 2006 1740
25. B. Beck, C.A. Leppert, B.K. Mueller, and A. Dömling QSAR Comb. Sci. 5 2006 127
26. V. Gracias, A.F. Gasiecki, and S.W. Djuric Tetrahedron Lett. 46 2005 9049
27. V. Gracias, D. Darczak, A.F. Gasiecki, and S.W. Djuric Tetrahedron Lett. 46 2005 9053
28. V. Gracias, A.F. Gasiecki, T.G. Pagano, and S.W. Djuric Tetrahedron Lett. 47 2006 8873
29. X. Beebe, V. Gracias, and S.W. Djuric Tetrahedron Lett. 47 2006 3225
30. For reviews describing the post-condensation modification approach see: L. Banfi, R. Riva, and A. Basso Synlett 1 2010 23
31. A. Basso, L. Banfi, and R. Riva Eur. J. Org. Chem. 2010 1831
32. R.S. Bon, C. Hong, M.J. Bouma, R.F. Schmitz, F.J.J. De Kanter, M. Lutz, A.L. Spek, and R.V.A. Orru Org. Lett. 5 2003 3759
33. N. Elders, R.F. Schmitz, E. Ruijter, M.B. Groen, and R.V.A. Orru J. Org. Chem. 72 2007 6135
34. R.S. Bon, N.E. Sprenkels, M.M. Koningstein, R.F. Schmitz, F.J.J. De Kanter, A. Dömling, and R.V.A. Orru Org. Biomol. Chem. 6 2008 130
35. For recent examples see: S. Gunawan, J. Petit, and C. Hulme ACS Comb. Sci. 14 2012 160
36. A.Y. Shaw, F. Medda, and C. Hulme Tetrahedron Lett. 53 2012 1313
37. S. Gunawan, M. Ayaz, F. De Moliner, B. Frett, C. Kaiser, N. Patrick, X. Zu, and C. Hulme Tetrahedron 68 2012 5606
38. S. Gunawan, K. Keck, A. Laetsch, and C. Hulme Mol. Divers. 2012 10.1007/s11030-012-9373-2
39. F. De Moliner, and C. Hulme Org. Lett. 14 2012 1354
40. Campbell, S. F.; Mackenzie, A. R.; Wood, A. WO 96/16644, 1996.
41. K.-H. Kim, A. Maderna, M.E. Schnute, M. Hegen, S. Mohan, J. Miyashiro, L. Lin, E. Li, S. Keegan, J. Lussier, C. Wrocklage, C.L. Nickerson-Nutter, A.J. Wittwer, H. Soutter, N. Caspers, S. Han, R. Kurumbail, K. Dunussi-Joannopoulos, J. Douhan III, and A. Wissner Bioorg. Med. Chem. Lett. 21 2011 6258
42. B.J. Stockman, M. Kothe, D. Kohls, L. Weibley, B.J. Connolly, A.L. Sheils, Q. Cao, A.C. Cheng, L. Yang, A.V. Kamath, Y.-H. Ding, and M.E. Charlton Chem. Biol. Drug. Des. 73 2009 179
43. Barrish, J. C.; Chen, P.; Das, J.; Iwanowicz, E. J.; Norris, D. J.; Padmanabha, R.; Roberge, J. Y.; Schieven, G. L. WO 99/09845, 1999.
44. P. Chen, D. Norris, E.J. Iwanovicz, S.H. Spergel, J. Lin, H.H. Gu, Z. Shen, J. Witjak, T.-A. Lin, S. Pang, H.F. De Fex, S. Pitt, D.R. Shen, A.M. Doweyko, D.A. Bassolino, J.Y. Roberge, M.A. Poss, B.-C. Chen, G.L. Schieven, and J.C. Barrish Bioorg. Med. Chem. Lett. 12 2002 1361
45. G. Moarbess, C. Deleuze-Masquefa, V. Bonnard, S. Gayraud-Paniagua, J.-R. Vidal, F. Bressolle, F. Pinguet, and P.-A. Bonnet Bioorg. Med. Chem. Lett. 16 2008 6601
46. Petasis, N. A.; Yao, X. U.S. Patent 0010162, 2004.
47. V. Colotta, L. Cecchi, D. Catarzi, G. Filacchioni, C. Martini, P. Tacchi, and A. Lucacchini Eur. J. Med. Chem. 30 1995 133
48. Hoefgen, N.; Stange, S.; Langen, B.; Egerlan, U.; Schindler, R. WO 09/068320, 2009.
49. Malamas, M. S.; Ni, Y.; Erdei, J. J.; Stange, S.; Schindler, R.; Hoefgen, N.; Egerlan, U.; Langen, B. WO 09/070584, 2009.