Generation of pyrrolo[2,1-a]isoquinoline derivatives from N-ylides: Synthetic control and structural characterization

Heteroatom Chemistry

Volumn 22, Issue 6, 2011, Pages 723-729

  Dumitrascu, Florea ^a   Caira, Mino R ^b   Georgescu, Emilian ^c   Georgescu, Florentina ^c   Draghici, Constantin ^a   Popa, Marcel Mirel ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

^c Oltchim Research Center   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80755139684     PISSN: 10427163     EISSN: 10981071     Source Type: Journal    
DOI: 10.1002/hc.20740     Document Type: Article

References (44)

1. Mikhailovskii, G.,;, Shklyaev, V. S., Chem Heterocyl Compd 1997, 33, 243-265
2. (b), Mikhailovskii, G.,;, Shklyaev, V. S., Khim Geterot Soedin 1997, 33, 291-317.
3. Yu, C.,;, Zhang, Y.,;, Zhang, S.,;, Li, H.,;, Wang, W., Chem Commun 2011, 47, 1036
4. (b), Voskressensky, L. G.,;, Listratova, A. L.,;, Bolshov, A. V.,;, Bizhko, O. K.,;, Borisova T. N.,;, Varlamov, A. V., Tetrahedron Lett 2010, 51, 840
5. (c), Tóth, J.,;, Váradi, L.,;, Dancsó, A.,;, Blaskó, G.,;, Töke, L.,;, Nyerges, M., Synthesis 2009, 41 (24), 4149.
6. (d), Verma, A. K.,;, Kesharwani, T.,;, Singh, J.,;, Tandon, V.,;, Larock, R. C., Angew Chem Int Ed 2009, 48, 1138
7. (e), Kianmehr, E.,;, Estiri, H.,;, Bahreman, A., J Heterocyclic Chem 2009, 46, 1203
8. (f), Yue, G.,;, Wan, Y.,;, Song, S.,;, Yang, G.,;, Chen, Z., Bioorg Med Chem Lett 2005, 15, 453.
9. Li, Q.,;, Jiang, J.,;, Fan, A.,;, Cui, Y.,;, Jia, Y., Org Lett 2011, 13, 312
10. (b), Shen, L.,;, Yang, X.,;, Yang, B.,;, He, Q.,;, Hu, Y., Eur J Med Chem 2010, 45, 11
11. (c), Yadav, J. S.,;, Gayathri, K. U.,;, Reddy, B. V. S.,;, Prasad, A. R., Synlett 2009, 20 (1), 43
12. (d), Liermann, J. C.,;, Opatz, T., J Org Chem 2008, 73, 4256
13. (e), Su, S.,;, Porco Jr., J. A., J Am Chem Soc 2007, 129, 7744
14. (f), Pla, D.,;, Marchal, A.,;, Olsen, C. A.,;, Albericio, F.,;, Alvarez, M., J Org Chem 2005, 70, 8231.
15. Yioti, E. G.,;, Mati, I. K.,;, Arvanitidis, A. G.,;, Massen, Z. S.,;, Alexandraki, E. S.,;, Gallos, J. K., Synthesis 2011, 43 (1), 142-146
16. (b), Knolker, H.-J.,;, Agarwal, S., Tetrahedron Lett 2005, 46, 1173
17. (c), Meyer, N.,;, Opatz, T.,; Eur J Org Chem 2006, 17, 3997
18. (d), Chiou, W.-H.,;, Lin, G.-H.,;, Hsu, C.-C.,;, Chaterpaul, S. J.,;, Ojima, I., Org Lett 2009, 11, 2659
19. (e), Opatz, T., Synthesis 2009, 1941.
20. Najera, C.,;, Sansano, J. M., Curr Org Chem 2003, 7, 1105-1150
21. (b), Peng, W.,;, Zhu, S., J Chem Soc Perkin Trans 1 2001, 23, 3204
22. (c), Liu, Y.,;, Hu, H.-Y.,;, Liu, Q.-J.,;, Hu, H.-W., Xu, J.-H., Tetrahedron 2007, 63, 2024.
23. Farnum, D. G.,;, Alaimo, R. J.,;, Dunston, J. M., J Org Chem 1967, 32, 1130.
24. Kutsuma, T.,;, Sekine, Y.,;, Fujiyama, K.,;, Kobayashi, Y., Chem Pharm Bull 1972, 20, 2701.
25. Dawood, K. M.,;, Ragab, E. A.,;, Khedr, N. A., J Chin Chem Soc 2009, 56, 1180.
26. Bacu, E.,;, Samson-Belei, D.,;, Nowogrocki, G.,;, Couture, A.,;, Grandclaudon, P., Org Biomol Chem 2003, 1, 2377.
27. Tsuge, O.,;, Kanemasa, S.,;, Takenaka, S., Bull Chem Soc Jpn 1985, 58, 3137
28. (b), Tsuge, O.,;, Kanemasa, S.,;, Sakamoto, K.,;, Takenaka, S., Bull Chem Soc Jpn 1988, 61, 3320
29. (c), Klamann, D.,;, Hageman H., "Organische Stickstoff-Verbindungen mit einer C, N Doppelbindung," Houben-Weyl, Thieme: Stuttgart, New York, 1991; E-14b, pp. 100-160.
30. (d), Dumitrascu, F.,;, Mitan, C. I.,;, Draghici, C.,;, Caproiu, M. T.,;, Raileanu, D., Tetrahedron Lett 2001, 42, 8379
31. (e), Dumitrascu, F.,;, Georgescu, E.,;, Caira, M. R.,;, Georgescu, F.,;, Popa, M.,;, Draghici, B.,;, Dumitrescu, D. G., Synlett 2009, 20 (20), 3336.
32. Georgescu, E.,;, Caira, M. R.,;, Georgescu, F.,;, Draghici, B.,;, Popa, M. M.,;, Dumitrascu, F., Synlett 2009, 20 (11), 1795
33. (b), Dumitrascu, F.,;, Caproiu, M. T.,;, Georgescu, F.,;, Draghici, B.,;, Popa, M. M.,;, Georgescu E., Synlett 2010, 21 (16), 2407
34. (c), Ramazani, A.,;, Ahmadi, Y.,;, Tarasi, R., Heteroat Chem 2011, 22, 79
35. (d), Rahmatpour, A.,;, Aalaie J., Heteroat Chem 2011, 22, 85.
36. Caira, M. R.,;, Georgescu, E.,;, Georgescu, F.,;, Albota, F.,;, Dumitrascu, F., Monat Chem 2011, Online First: DOI: 10.1007/s00706-011-0468-8.
37. Dumitrascu, F.,;, Caira, M. R.,;, Draghici, C.,;, Caproiu, M.T.,;, Barbu, L., Rev Chim (Bucharest) 2009, 60, 851.
38. Wei, X.,;, Hu, Y.,;, Li, T.,;, Hu, H., J Chem Soc Perkin Trans 1 1993, 2487
39. (b), Zhou, J.,;, Hu, Y.,;, Hu, H., J Heterocyclic Chem 2000, 37, 1165
40. (c), Wang, B.,;, Hu, J.,;, Zhang, X.,;, Hu, Y.,;, Hu, H., J Heterocyclic Chem 2000, 37, 1533.
41. Hooft, R.,;, Nonius, B. V., Collect: Data Collection Software;, Hooft, R.,;, Nonius B. V., (Eds.); Delft, The Netherlands, 2000.
42. Otwinowski, Z.,;, Minor, W., Methods Enzymol 1997, 276, 307.
43. Sheldrick, G. M., SHELXS-97; University of Göttingen: Germany, 1997.
44. Sheldrick, G. M., SHELXL-97; University of Göttingen: Germany, 1997.