Efficient synthesis of 2-substituted 7-azaindole derivatives via palladium-catalyzed coupling and C-N cyclization using 18-crown-6

Synthesis

Volumn , Issue 14, 2007, Pages 2149-2152

  De Mattos, Marcos Carlos ^a   Alatorre Santamaría, Sergio ^a   Gotor Fernández, Vicente ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

18 crown 6; 7 azaindoles; Alkynes; Heterocycles; Palladium catalysis

Indexed keywords

ALKYNES; AZAINDOLES; IODOPYRIDINES; PALLADIUM CATALYSIS;

AMINO ACIDS; CATALYSIS; CROWN ETHERS; DERIVATIVES; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

2 AMINO 3 IODOPYRIDINE; 7 AZAINDOLE DERIVATIVE; CROWN COMPOUND; DECANE; INDOLE DERIVATIVE; PALLADIUM; PYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SONOGASHIRA REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34547183435     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983730     Document Type: Article

References (26)

1. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry, Vol. 4; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, 313.
2. (a) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
3. (b) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
4. See for example: (a) Tani, K.; Sakurai, H.; Fujii, H.; Hirao, T. J. Organomet. Chem. 2004, 689, 1665.
5. (b) Zhao, S.-B.; Song, D.; Jia, W.-L.; Wang, S. Organometallics 2005, 24, 3290; and references cited therein.
6. (a) Zhang, H.-C.; Ye, H.; Conway, B. R.; Derian, C. K.; Addo, M. F.; Kuo, G.-H.; Hecker, L. R.; Croll, D. R.; Li, J.; Westover, L.; Xu, J. Z.; Look, R.; Demarest, K. T.; Andrade-Gordon, P.; Damiano, B. P.; Maryanoff, B. E. Bioorg. Med. Chem. Lett. 2004, 14, 3245.
7. (b) Larraya, C.; Guillard, J.; Renard, P.; Audinot, V.; Boutin, J. A.; Delagrange, P.; Bennejean, C.; Viaud-Massuard, M.-C. Eur. J. Med. Chem. 2004, 12, 5505.
8. (c) Fonquerna, S.; Miralpeix, M.; Pagès, L.; Puig, C.; Cardús, A.; Antón, F.; Villela, D.; Aparici, M.; Prieto, J.; Warrellow, G.; Beleta, J.; Ryder, H. Bioorg. Med. Chem. Lett. 2005, 15, 1165.
9. (d) Messaoudi, S.; Anizon, F.; Pfeiffer, B.; Proudhomme, M. Tetrahedron 2005, 61, 7304.
10. (e) Guillard, J.; Decrop, M.; Gallay, N.; Espanel, C.; Boissier, E.; Herault, O.; Viaud-Massuard, M.-C. Bioorg. Med. Chem. Lett. 2007, 17, 1934.
11. (f) Bahekar, R. H.; Jain, M. R.; Goel, A.; Patel, D. N.; Prajapati, V. M.; Gupta, A. A.; Jadap, P. A.; Patel, P. R. Bioorg. Med. Chem. 2007, 15, 3248.
12. (a) Popowycz, F.; Routier, S.; Joseph, B.; Merour, J.-Y. Tetrahedron 2006, 63, 1031.
13. (b) Schirok, H.; Figueroa-Pérez, S.; Thutewol, M.; Paulsen, H.; Kroh, W.; Klewer, D. Synthesis 2007, 251.
14. (c) Caldwell, J. J.; Cheung, K.-M.; Collins, I. Tetrahedron Lett. 2007, 48, 1527.
15. Clemo, G. R.; Swan, G. A. J. Chem. Soc. 1945, 603.
16. Houlihan, W. J.; Parrino, V. A.; Uike, Y. J. Org. Chem. 1981, 46, 4511.
17. (a) Estel, L.; Marsais, F.; Quéguiner, G. J. Org. Chem. 1988, 53, 2740.
18. (b) Davis, M. L.; Wakefield, B. J.; Wardell, J. A. Tetrahedron 1992, 48, 939.
19. (c) Rodríguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem. Int. Ed. 2000, 39, 2488.
20. (d) Koradin, C.; Dohle, W.; Rodríguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
21. (a) Clark, R. D.; Muchowski, J. M.; Fisher, L. E.; Flippin, L. A.; Repke, D. B.; Souchet, M. Synthesis 1991, 871.
22. (b) Park, S. S.; Choi, J.-K.; Yum, E. K. Tetrahedron Lett. 1998, 39, 627.
23. (c) Hong, C. S.; Seo, J. Y.; Yum, E. K.; Sung, N.-D. Heterocycles 2004, 63, 631.
24. (d) McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3307.
25. Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527.
26. Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529.