Efficient synthesis of imidazopyridodiazepines from peri annulation in imidazo[1,2-a]pyridine

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9119-9123

  Dechambre, C ^a   Chezal, Jean M ^a   Moreau, E ^a   Estour, F ^b   Combourieu, B ^c   Grassy, G ^d   Gueiffier, A ^e   Enguehard, C ^e   Gaumet, V ^a   Chavignon, Olivier ^a   Teulade, Jean C ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b UNIVERSITÉ DE ROUEN   (France)

^c CNRS   (France)

^d INSERM   (France)

^e UNIVERSITÉ DE TOURS   (France)

Author keywords

Imidazopyridodiazepine; Imidazo 1,2 a pyridine; Mechanism; peri annulation

Indexed keywords

BENZODIAZEPINE DERIVATIVE; DIAZEPINE DERIVATIVE; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; INDOLE DERIVATIVE; NEVIRAPINE; POLYCYCLIC HYDROCARBON; TIVIRAPINE; UK 129485; UNCLASSIFIED DRUG;

ANNULATION; ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0037049206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02239-6     Document Type: Article

References (31)

1. De Clercq E. Il Farmaco. 54:1999;26-45.
2. De Clercq E. Il Farmaco. 56:2001;3-12.
3. Kukla M.J., Breslin H.J., Diamond C.J., Grous P.P., Ho C.Y., Miranda M., Rodgers J.D., Sherrill R.G., De Clercq E., Pauwels R., Andries K., Moens L., Janssen M.A., Janssen P.A. J. Med. Chem. 34:1991;3187-3197.
4. Breslin H.J., Kukla M.J., Ludovici D.W., Mohrbacher R., Ho W., Miranda M., Rodgers J.D., Hitchens T.K., Leo G., Gauthier D.A., Ho C.Y., Scott M.K., De Clercq E., Pauwels R., Andries K., Janssen M.A., Janssen P.A. J. Med. Chem. 38:1995;771-793.
5. Salaski E.J. Tetrahedron Lett. 36:1995;1387-1390.
6. Ho W., Kukla M.J., Breslin H.J., Ludovici D.W., Grous P.P., Diamond C.J., Miranda M., Rodgers J.D., Ho C.Y., De Clercq E., Pauwels R., Andries K., Janssen M.A., Janssen P.A. J. Med. Chem. 38:1995;794-802.
7. Chezal J.M., Moreau E., Chavignon O., Gaumet V., Métin J., Blache Y., Diez A., Fradera X., Luque J., Teulade J.C. Tetrahedron. 58:2002;295-297.
8. 3: C, 78.86; H, 6.62; N, 14.52. Found: C, 78.95; H, 6.59; N, 14.46.
9. Soerens D., Sandrin J., Ungemach F., Mokry P., Wu G.S., Yamanaka E., Hutchins L., DiPierro M., Cook J.M. J. Org. Chem. 44:1979;535-545.
10. Jawdosiuk M., Cook J.M. J. Org. Chem. 49:1984;2699-2701.
11. Narayanan K., Cook J.M. Tetrahedron Lett. 31:1990;3397-3400.
12. Mokrosz M.J., Kowalski P., Bojarski A.J., Mokrosz J.L. Heterocycles. 37:1994;265-274.
13. Novk L., Hanania M., Kovàcs P., Rohàly J., Kolonits P., Szàntay C. Heterocycles. 45:1997;2331-2348.
14. Liu J., Nakagawa M., Hino T. Tetrahedron. 45:1989;7729-7742.
15. Czerwinski K.M., Deng L., Cook J.M. Tetrahedron Lett. 33:1992;4721-4724.
16. Jackson A.H., Naidoo B., Smith P. Tetrahedron. 24:1968;6119-6129.
17. Ungemach F., Soerens D., Weber R., DiPierro M., Campos O., Mokry P., Cook J.M., Silverton J.V. J. Am. Chem. Soc. 102:1980;6976-6984.
18. Plate R., Van Hout R.H.M., Behm H., Ottenheijm H.J. J. Org. Chem. 52:1987;555-560.
19. Narayanan K., Schindler L., Cook J.M. J. Org. Chem. 56:1991;359-365.
20. Borrows E.T., Holland D.O., Kenyon J. J. Chem. Soc. 1946;1075-1089.
21. Potts K.T., Burton H.R. Proc. Chem. Soc. 1964;420-421.
22. Partridge M.W., Stevens M.F.G. J. Chem. Soc. C. 1967;1828-1830.
23. Irwin W.J., Wibberley D.G. J. Chem. Soc. C. 1971;3237-3239.
24. Birch D.J., Guildford A.J., Tometzki M.A., Turner R.W. J. Org. Chem. 47:1982;3547-3548.
25. Teulade J.C., Escale R., Viols H., Chapat J.P., Grassy G., Carpy A., Léger J.M. J. Chem. Soc., Perkin Trans. 1. 1983;2663-2667.
26. Crystallographic data (excluding structure factors) for the structure 6a in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications number CCDC 193333. Copies of the data can be obtained, free of charge, on application to CCDC 193333, 12 Union Road, Cambrige, CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
27. Srivastava P., Pandey V.C., Misra A., Gupta P., Raj K., Bhaduri A.P. Bioorg. Med. Chem. 6:1998;181-187.
28. Grassy G., Teulade J.C., Chapat J.P., Simeon de Buochberg M., Attisso M. Eur. J. Med. Chem. Chim. Ther. 17:1982;109-115.
29. Roe A.M. J. Chem. Soc. 1963;2195-2200.
30. Mandereau J., NguyenTri-Xuong E., Reynaud P. Eur. J. Med Chem. Chim. Ther. 9:1974;344-346.
31. 3: C, 77.25; H, 8.53; N, 14.22. Found: C, 77.21; H, 8.54; N, 14.25.