Microwave-assisted synthesis of indolizino[1,2-b]quinolines

Synlett

Volumn , Issue 12, 2002, Pages 2077-2079

  Perzyna, Aurore ^a   Houssin, Raymond ^a   Barbry, Didier ^b   Hénichart, Jean Pierre ^a  

^a Faculté des Sciences Pharmaceutiques et Biologiques Université de Lille   (France)

^b UNIV LILLE   (France)

Author keywords

Friedl nder reaction; Indolizinoquinoline; Microwave irradiation

Indexed keywords

BENZALDEHYDE DERIVATIVE; INDOLIZINE DERIVATIVE; INDOLIZINO[1,2 B]QUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE RADIATION; SYNTHESIS;

EID: 0036456012     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35585     Document Type: Article

References (23)

1. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; Mc Phail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1966, 88, 3888.
2. Govindachari, T. R.; Ravindranath, K. R.; Viswanathan, N. J. Chem. Soc., Perkin Trans. 1 1974, 1215.
3. (a) Bergstrom, F. V. Chem. Rev. 1948, 48, 47.
4. (b) Lauer, W. M.; Kaslow, C. E. In Org. Synth., Coll. Vol. III; Horning, E. C., Ed.; Wiley: New York, 1955, 580.
5. Manske, R. H. F.; Kulka, M. In Organic Reactions, Vol. 7; Adams, R., Ed.; Wiley: New York, 1953.
6. (a) Elderfield, R. C. In Heterocyclic Compounds, Vol. 4; Elderfield, R. C., Ed.; Wiley: New York, 1952, 45.
7. (b) Ubeda, J. I.; Villacampa, M.; Avendano, C. Synthesis 1998, 1176.
8. Sugimori, M.; Ejima, A.; Ohsuki, S.; Uoto, K.; Mitsui, I.; Matsumoto, K.; Kawato, Y.; Yasuoka, M.; Sato, K.; Tagawa, H.; Terasawa, H. J. Med. Chem. 1994, 37, 3033.
9. For papers on microwave utilization see: (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225. (b) Caddick, S. Tetrahedron 1995, 51, 10403. (c) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665. (d) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquaut, P.; Mathé D. Synthesis 1998, 1213. (e) Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027. (f) Cablewski, T.; Faux, A. F.; Srauss, C. R. J. Org. Chem. 1994, 59, 3408.
10. For papers on microwave utilization see: (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225. (b) Caddick, S. Tetrahedron 1995, 51, 10403. (c) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665. (d) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquaut, P.; Mathé D. Synthesis 1998, 1213. (e) Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027. (f) Cablewski, T.; Faux, A. F.; Srauss, C. R. J. Org. Chem. 1994, 59, 3408.
11. For papers on microwave utilization see: (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225. (b) Caddick, S. Tetrahedron 1995, 51, 10403. (c) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665. (d) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquaut, P.; Mathé D. Synthesis 1998, 1213. (e) Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027. (f) Cablewski, T.; Faux, A. F.; Srauss, C. R. J. Org. Chem. 1994, 59, 3408.
12. For papers on microwave utilization see: (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225. (b) Caddick, S. Tetrahedron 1995, 51, 10403. (c) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665. (d) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquaut, P.; Mathé D. Synthesis 1998, 1213. (e) Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027. (f) Cablewski, T.; Faux, A. F.; Srauss, C. R. J. Org. Chem. 1994, 59, 3408.
13. For papers on microwave utilization see: (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225. (b) Caddick, S. Tetrahedron 1995, 51, 10403. (c) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665. (d) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquaut, P.; Mathé D. Synthesis 1998, 1213. (e) Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027. (f) Cablewski, T.; Faux, A. F.; Srauss, C. R. J. Org. Chem. 1994, 59, 3408.
14. For papers on microwave utilization see: (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225. (b) Caddick, S. Tetrahedron 1995, 51, 10403. (c) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665. (d) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquaut, P.; Mathé D. Synthesis 1998, 1213. (e) Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027. (f) Cablewski, T.; Faux, A. F.; Srauss, C. R. J. Org. Chem. 1994, 59, 3408.
15. 13 (2.6 mmol) were added to acetic acid (20 mL) and heated while stirring under reflux for 8 h (TLC control). The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product was diluted in methanol and hydrogen chloride was bubbled. The products were purified by flash chromatography (dichloromethanemethanol 8:2→7:3) before recrystallization.
16. 2O: C, 60.17; H, 6.80; N, 10.79; C1, 6.83. Found: C, 60.03; H, 7.05; N, 10.41; C1, 7.12.
17. Chemat, F.; Esveld, E. Chem. Eng. Technol. 2001, 24, 735.
18. (a) Wani, M. C.; Ronman, P. E.; Lindley, J. T.; Wall, M. E. J. Med. Chem. 1980, 23, 554.
19. (b) Wall, M. E.; Wani, M. PCT Int. Appl. WO 91/05556, 1991; Chem. Abstr. 1991, 115, 92686x.
20. (b) Wall, M. E.; Wani, M. PCT Int. Appl. WO 91/05556, 1991; Chem. Abstr. 1991, 115, 92686x.
21. Perzyna, A.; Marty, C.; Facompré, M.; Goossens, J.-F.; Pommery, N.; Colson, P.; Houssier, C.; Houssin, R.; Hénichart, J.-P.; Bailly, C. J. Med. Chem., accepted for publication.
22. (a) Borsche, W.; Doeller, W.; Wagner-Roemmich, M. Chem. Ber. 1943, 76, 1099.
23. (b) Jonhston, D.; Smith, D. M.; Sheperd, T.; Thompson, D. J. Chem. Soc., Perkin Trans. 1 1987, 495.