A short and convenient synthesis of 3-aminomethyl-5-imino-8-nitro-2,3- dihydroimidazo[1,2-a]pyridines

Synthesis

Volumn , Issue 12, 2006, Pages 2031-2038

  Schmid, Sylvia ^a   Schühle, Daniel ^a   Austel, Volkhard ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

Amines; Bicyclic compounds; Combinatorial chemistry; Nucleophilic aromatic substitution; Ring opening

Indexed keywords

AMINES; CARBOXYLIC ACIDS; MEDICINE; SYNTHESIS (CHEMICAL);

BICYCLIC COMPOUNDS; COMBINATORIAL CHEMISTRY; NUCLEOPHILIC AROMATIC SUBSTITUTION; RING OPENING;

ORGANIC COMPOUNDS;

3 AMINOMETHYL 5 IMINO 8 NITRO 2,3 DIHYDROIMIDAZO[1,2 A]PYRIDINE DERIVATIVE; 3 ANILINOMETHYL 5 BENZYLIMINO 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 3 ANILINOMETHYL 5 CYCLOHEXYLIMINO 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 3 ANILINOMETHYL 5 PHENYLIMINO 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 3 BENZYLAMINOMETHYL 5 (4 PIPERIDYLMETHYL)IMINO 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 3 BENZYLAMINOMETHYL 5 BENZYLIMINO 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 3 BENZYLAMINOMETHYL 5 CYCLOHEXYLIMINO 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 3 BENZYLAMINOMETHYL 5 PHENYLIMINO 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 5 BENZYLIMINO 3 (3 METHOXYANILINOMETHYL) 8 NITRO 1,2,3,5 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; AMINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL REACTION; COMBINATORIAL LIBRARY; DRUG STRUCTURE; DRUG SYNTHESIS; MATRIX ATTACHMENT REGION;

EID: 33745756388     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942391     Document Type: Article

References (36)

1. Schmid, S. PhD Thesis; University of Ulm: Germany, 2005.
2. (a) Hamdouchi, C.; de Blas, J.; del Prado, M.; Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.
3. (b) Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.-C; Witvrouw, M.; Balzarini, J.; De Clercq, E.; Chapat, J.-P. J. Med. Chem. 1998, 41, 5108.
4. (c) Gueiffier, A.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.-C.; Kerbal, A.; Essassi, E. M.; Debouzy, J.-C.; Witvrouw, M.; Blache, Y.; Balzarini, J.; De Clercq, E.; Chapat, J.-P. J. Med. Chem. 1996, 39, 2856.
5. Fisher, M. H.; Lusi, A. J. Med. Chem. 1972, 15, 982.
6. Grassy, G.; Teulade, J.-C.; Chapat, J.-P.; de Buochberg, M. S.; Attiso, M. Eur. J. Med. Chem. 1982, 17, 109.
7. Abe, Y.; Kayakiri, H.; Satoh, S.; Inoue, T.; Sawada, Y.; Imai, K.; Inamura, N.; Asano, M.; Hatori, C.; Katayama, A.; Oku, T.; Tanaka, H. J. Med. Chem. 1998, 41, 564.
8. Sanfilippo, P. J.; Urbanski, M.; Press, J. B.; Dubinsky, B.; Moore, J. B. J. Med. Chem. 1988, 31, 2221.
9. Spitzer, W. A.; Viktor, F.; Pollock, G. D.; Hayes, J. S. J. Med. Chem. 1988, 31, 1590.
10. Davey, D.; Erhardt, P. W.; Lumma, W. C.; Wiggins, J.; Sullivan, M.; Pang, D.; Cantor, E. J. Med. Chem. 1987, 30, 1337.
11. Meyer, H.; Bossert, F.; Vater, W.; Stoepel, K. Ger. Offen. 2406199, 1975; Chem. Abstr. 1975, 83, 193374.
12. (a) Kaminski, J. J.; Perkins, D. G.; Frantz, J. D.; Solomon, D. M.; Elliott, A. J.; Chiu, P. J. S.; Long, J. F. J. Med. Chem. 1987, 30, 2047.
13. (b) Kaminski, J. J.; Hilbert, J. M.; Pramanik, B. N.; Solomon, D. M.; Conn, D. J.; Rizvi, R. K.; Elliott, A. J.; Guzik, H.; Lovey, G. R.; Domalski, M. S.; Wong, S.-C.; Puchalski, C.; Gold, E. H.; Long, J. F.; Chiu, P. J. S.; McPhail, A. T. J. Med. Chem. 1987, 30, 2031.
14. (c) Kaminski, J. J.; Bristol, J. A.; Puchalski, C.; Lovey, G. R.; Elliott, A. J.; Guzik, H.; Solomon, D. M.; Conn, D. J.; Domalski, M. S.; Wong, S.-C.; Gold, E. H.; Long, J. F.; Chiu, P. J. S.; Steinberg, M.; McPhail, A. T. J. Med. Chem. 1985, 28, 876.
15. (a) Trapani, G.; Laquintana, V.; Denora, N.; Trapani, A.; Lopedota, A.; Latrofa, A.; Franco, M.; Serra, M.; Pisu, M. G.; Floris, I.; Sanna, E.; Biggio, G.; Liso, G. J. Med. Chem. 2005, 48, 292.
16. (b) Cai, G.; Albaugh, P.; Shaw, K. PCT Appl. WO 0192257, 2001; Chem. Abstr. 2001, 136, 20071.
17. (c) Trapani, G.; Franco, M.; Latrofa, A.; Ricciardi, L.; Carotti, A.; Serra, M.; Sanna, E.; Biggio, G.; Liso, G. J. Med. Chem. 1999, 42, 3934.
18. Almirante, L.; Polo, L.; Mugnaini, A.; Provinciali, E.; Rugarli, P.; Biancotti, A.; Gamba, A.; Murmann, W. J. Med. Chem. 1965, 8, 305.
19. (a) Kubo, K.; Itoh, N.; Sozu, I.; Isomura, Y.; Homma, H.; Murakami, M. Brit. Patent 1588166, 1981; Chem. Abstr. 1982, 96, 68987.
20. (b) Kubo, K.; Ito, N.; Isomura, Y.; Sozu, I.; Homma, H.; Murakami, M. Chem. Pharm. Bull. 1979, 27, 1207.
21. (c) Kubo, K.; Ito, N.; Isomura, Y.; Sozu, I.; Homma, H.; Murakami, M. Yakugaku Zasshi 1979, 99, 880;
22. Chem. Abstr. 1980, 92, 58685.
23. (d) Kubo, K.; Itoh, N.; Sozu, I.; Isomura, Y.; Homma, H. Jpn. Kokai 54005997, 1979; Chem. Abstr. 1979, 91, 193225.
24. (e) Kubo, K.; Itoh, N.; Sozu, I.; Isomura, Y.; Homma, H.; Murakami, M. Ger. Offen. 2731982, 1978; Chem. Abstr. 1978, 88, 136596.
25. Kayakiri, H.; Takase, S.; Shibata, T.; Okamoto, M.; Terano, H.; Hashimoto, M.; Tada, T.; Koda, S. J. Org. Chem. 1989, 54, 4015.
26. Shiokawa, K.; Tsuboi, S.; Sasaki, S.; Moriya, K.; Hattori, Y.; Shibuya, K. Eur. Pat. Appl. EP 296435, 1988; Chem. Abstr. 1989, 111, 7424.
27. Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226.
28. Schmid, S.; Schühle, D.; Steinberger, S.; Xin, Z.; Austel, V. Synthesis 2005, 3107.
29. (a) Schäfer, H.; Gruner, M.; Großmann, G.; Gewald, K. Monatsh. Chem. 1991, 959.
30. (b) Schäfer, H.; Gewald, K. Z. Chemie 1978, 18, 335.
31. Hehemann, D. G.; Winnik, W. J. Heterocycl. Chem. 1994, 31, 393.
32. Cossey, A. L.; Harris, R. L. N.; Huppatz, J. L. Aust. J. Chem. 1976, 29, 1039.
33. Winnik, H. J. Heterocycl. Chem. 1995, 32, 477.
34. Dehnert, J.; Lamm, G. Ger. Offen. 2022817, 1972; Chem. Abstr. 1972, 76, 142405.
35. Podhorez, D. E. J. Heterocycl. Chem. 1991, 28, 971.
36. Parenty, A. D. C.; Smith, L. V.; Cronin, L. Tetrahedron 2005, 61, 8410.