First synthesis of 4-aminopyrido[2′,3′:4,5]furo[3,2-d] pyrimidines

Tetrahedron Letters

Volumn 53, Issue 8, 2012, Pages 944-947

  Loidreau, Yvonnick ^a   Marchand, Pascal ^b   Dubouilh Benard, Carole ^a   Nourrisson, Marie Renée ^b   Duflos, Muriel ^b   Besson, Thierry ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DE NANTES   (France)

Author keywords

Dimroth rearrangement; Microwave assisted chemistry; Pyrido 2 ,3 :4,5 furo 3,2 d pyrimidines

Indexed keywords

4 AMINOPYRIDINE DERIVATIVE; AMINE; FURAN DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; MICROWAVE IRRADIATION; REACTION ANALYSIS; SYNTHESIS; TECHNOLOGY;

EID: 84855945583     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.042     Document Type: Article

References (23)

1. A. Testard, L. Picot, O. Lozach, M. Blairvac, L. Meijer, L. Murillo, J.-M. Piot, V. Thiéry, and T. Besson J. Enzym. Inhib. Med. Chem. 20 2005 557 568
2. A. Testard, C. Logé, B. Léger, J.-M. Robert, O. Lozach, M. Blairvacq, L. Meijer, V. Thiéry, and T. Besson Bioorg. Med. Chem. Lett. 16 2006 3419 3423
3. C. Logé, A. Testard, V. Thiéry, O. Lozach, M. Blairvacq, J.-M. Robert, L. Meijer, and T. Besson Eur. J. Med. Chem. 43 2008 1469 1477
4. M. Antoine, M. Czech, M. Gerlach, E. Günther, T. Schuster, and P. Marchand Synthesis 5 2011 794 806
5. A. Bretéché, P. Marchand, M.-R. Nourrisson, P. Hautefaye, G. De Nanteuil, and M. Duflos Tetrahedron 67 2011 4767 4773
6. A. Bretéché, P. Marchand, M.-R. Nourrisson, G. De Nanteuil, and M. Duflos Tetrahedron 66 2010 4490 4494
7. Wang, C. -C.; Liu, C. -F.; Lee, K. -Y.; Lin, M. -C.; Wang, S. -H.; Yen, C. -F.; Wang, Y. -H.; King, R. C. -H. U.S. 20110178107 A1, 2011; Chem. Abstr. 2011, 155, 212110.
8. M. Hayakawa, H. Kaizawa, H. Morimoto, T. Koizumi, T. Ohishi, M. Yamano, M. Okada, M. Ohta, S. Tsukamato, F.I. Raynaud, P. Workman, M.D. Waterfield, and P. Paker Bioorg. Med. Chem. Lett. 17 2007 2438 2442
9. Hayakawa, M.; Kaizawa, H.; Morimoto, H.; Kawaguchi, K.; Koizumi, T.; Yamano, M.; Matsuda, K.; Okada, M.; Ohta, M.; WO 2001083456 A1;Chem. Abstr. 2001, 135, 344500.
10. G. Wagner, J. Prantz, and S. Leistner Pharmazie 47 1992 825 828
11. Shuttleworth, S. S.; Cecil, A. R. L.; Hill, T. J.; Silva, F. A. WO 2011,021,038 A1; Chem. Abstr. 2011, 154, 284313.
12. O. Dimroth Liebigs Ann. Chem. 364 1909 183 226 This paper is considered as the first paper of Otto Dimroth reporting the translocation of endocyclic and exocyclic nitrogen atoms with certain 1,2,3-triazoles.
13. For two very complete reviews on Dimroth rearrangement see: E.S.H. El Ashry, S. Nadeem, M. Raza Shah, and Y. El Kilany Adv. Heterocycl. Chem. 101 2010 161 229
14. E.S.H. El Ashry, Y. El Kilany, N. Rashed, and H. Assafir Adv. Heterocycl. Chem. 75 1999 79 165
15. Hurley, L. H.; Mahadevan, D.; Han, H.; Bearss, D. J.; Vankayalapati, H.; Bashyam, S.; Munoz, R. M.; Warner, S. L.; Della Croce, K.; Von Hoff, D. D.; Grand, C. L.; Welsh, J. (a) U.S. 20090099165 A1; Chem. Abstr. 2009, 150, 414245;
16. (b) U.S. Patent 20090143399 A1; Chem. Abstr. 2009, 151, 8539.
17. V. Koch, and S. Schnatterer Synthesis 1990 497 498
18. For a paper on the thermal effect of microwaves see: D. Obermayer, B. Guttmann, and C.O. Kappe Angew. Chem., Int. Ed. 48 2009 8321 8324
19. Lost dissipation factor (tan δ) expresses the capacity of a molecule or a material to transform electromagnetic energy into thermal energy. A high susceptibility to microwaves is characterized by a high value (>0.5) of tan δ. For more details see: C. Gabriel, S. Gabriel, E.J. Grant, B.S. Halstead, and D.M.P. Mingos Chem. Soc. Rev. 27 1998 213 223
20. Y. Loidreau, and T. Besson Tetrahedron 67 2011 4852 4857
21. H.R. Tsou, N. Mamuya, B.D. Johnson, M.F. Reich, B.C. Gruber, F. Ye, R. Nilakantan, R. Shen, C. Discafani, R. DeBlanc, R. Davis, R.E. Koehn, L.M. Greenberger, Y.F. Wang, and A. Wissner J. Med. Chem. 44 2001 2719 2734
22. D.S. Yoon, H. Han, T.M. Stark, J.C. Haber, B.T. Gregg, and S.B. Stankovich Org. Lett. 6 2004 4775 4778
23. A. Foucourt, C. Dubouilh-Benard, E. Chosson, C. Corbire, C. Buquet, M. Iannelli, B. Leblond, F. Marsais, and T. Besson Tetrahedron 66 2010 4495 4502