A simple two-step sequence for the synthesis of novel 4-aryl-4,5-dihydro- 6H-[1,3]dioxolo[4,5-h]pyrrolo[1,2-a][1]benzazepin-6-ones from 6-amino-3,4-methylenedioxyacetophenone

European Journal of Organic Chemistry

Volumn , Issue 27, 2008, Pages 4684-4689

  Abonia, Rodrigo ^a   Cuervo, Paola ^a   Insuasty, Braulio ^a   Quiroga, Jairo ^a   Nogueras, Manuel ^b   Cobo, Justo ^b  

^a UNIVERSIDAD DEL VALLE   (Colombia)

^b UNIVERSITY OF JAÉN   (Spain)

Author keywords

Chalcones; Cyclization; Heterocycles; Michael addition; Phosphoric acid

Indexed keywords

EID: 53849137353     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800493     Document Type: Article

References (26)

1. a) A. Guzikowsky, S. Espitia, J. Hawkinson, J. Huettner, D. Nogales, R. Wodward, E. Weber, C. Keana, J. Med. Chem. 1996, 39, 4643-4653;
2. b) A. Link, C. Kunick, J. Med. Chem. 1998, 41, 1299-1305.
3. a) J. García, J. Andrés, A. Fraile, A. Martín, M. Martín, Tetrahedron Lett. 2004, 45, 4653-4656;
4. b) M. Novikov, A. Khlebnikov, M. Shevchenko, J. Fluorine Chem. 2003, 123, 177-181;
5. c) G. Campiani, A. Ramunno, I. Fiorini, V. Nacci, E. Morelli, E. Novellino, M. Goegan, T. Mennini, S. Sullivan, D. Zisterer, C. Williams, J. Med. Chem. 2002, 45, 4276-4281;
6. d) G. Milligan, C. Mossman, J. Aube, J. Am. Chem. Soc. 1995, 117, 10449-10459;
7. e) M. Ikeda, S. Akamatsu, Y. Kugo, T. Sato, Heterocycles 1996, 42, 155-158;
8. f) L. Huang, Z. Xue in The Alakaloids (Ed.: A. Brossi), Academic Press, New York, 1984, vol. 23, pp. 157-226;
9. g) M. Jalil Miah, T. Hudlicky, J. Reed in The Alakaloids (Ed.: A. Brossi), AcademicPress, New York, 1998, vol. 51, pp. 199-269;
10. h) P. Benderra, H. Morjani, A. Trussardi, M. Manfait, Leukemia 1998, 12, 1539-1544;
11. i) S. Sacchi, H. Kantarjian, S. O'Brien, J. Cortes, M. Rios, F. Giles, M. Beran, C. Koller, M. Keating, M. Talpaz, Cancer 1999, 86, 2632-2641;
12. j) L. Tietze, H. Braun, P. Steck, S. El Bialy, N. Tölle, A. Düfert, Tetrahedron 2007, 63, 6437-6445;
13. k) J. Koseki, H. Sato, Y. Watanabe, T. Nagasaka, Org. Lett. 2002, 4, 885-888;
14. l) E. de Oliveira, F. Dumas, J. d'Angelo, Tetrahedron Lett. 1997, 38, 3723-3726.
15. a) J. Low, J. Cobo, M. Nogueras, P. Cuervo, R. Abonia, Ch. Glidewell, Acta Crystallogr., Sect. C 2004, 60, 744-750;
16. b) J. Low, J. Cobo, P. Cuervo, R. Abonia, Ch. Glidewell, Acta Crystallogr., Sect. C 2004, 60, 827-829;
17. c) J. Low, J. Cobo, A. Ortíz, P. Cuervo, R. Abonia, Ch. Glidewell, Acta Crystallogr., Sect. E 2004, 60, 1057-1059;
18. d) J. Low, J. Cobo, M. Nogueras, A. Sánchez, A. Albornoz, R. Abonia, Acta Crystallogr., Sect. E 2002, 58, 42-45;
19. e) P. Cuervo, R. Abonia, J. Cobo, J. Low, Ch. Glidewell, Acta Crystallogr., Sect. C 2007, 63, 99-101;
20. f) R. Abonia, P. Cuervo, B. Insuasty, J. Quiroga, M. Nogueras, J. Cobo, H. Meier, E. Lotero, Open Org. Chem. J. 2008, 2, 26-34.
21. a) G. Cheeseman, M. Rafiq, J. Chem. Soc. C 1971, 2732-2734;
22. b) S. Raines, S. Chai, F. Palopoli, J. Heterocycl. Chem. 1976, 13, 711-716;
23. c) S. Massa, A. Mai, R. Di Santo, M. Artico, J. Heterocycl. Chem. 1993, 30, 897-903;
24. d) F.-W. Sum, J. Dusza, E. Delos Santos, G. Grosu, M. Reich, X. Du, J. Albright, P. Chan, J. Coupet, X. Ru, H. Mazandarani, T. Saunders, Bioorg. Med. Chem. Lett. 2003, 13, 2195-2198;
25. e) R. Abonia, B. Insuasty, J. Quiroga, H. Kolshorn, H. Meier, J. Heterocycl. Chem. 2001, 38, 671-674.
26. M. Banwell, D. Beck, J. Smith, Org. Biomol. Chem. 2004, 2, 157-159.