Zn-mediated synthesis of 3-substituted indoles using a three-component reaction approach

European Journal of Inorganic Chemistry

Volumn , Issue 29, 2012, Pages 4694-4700

  Anselmo, Daniele ^a   Escudero Adán, Eduardo C ^b   Martínez Belmonte, Marta ^b   Kleij, Arjan W ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

Homogeneous catalysis; Multicomponent reactions; Nitrogen heterocycles; Salphen ligands; Zinc

Indexed keywords

CATALYSIS; CHELATION; REACTION INTERMEDIATES; ZINC COMPOUNDS;

BENZYLIDENE; HOMOGENEOUS CATALYSIS; MALONONITRILES; MULTICOMPONENT REACTION; MULTICOMPONENTS; NITROGEN HETEROCYCLES; SALPHEN LIGAND; SUBSTITUTED INDOLES; THREE COMPONENT REACTIONS; ZINC;

NITROGEN;

EID: 84864235955     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201200150     Document Type: Conference Paper

References (33)

1. I. Ugi, A. Dömling, B. J. Werner, Heterocycl. Chem. 2000, 37, 647.
2. I. Ugi, R. Meyr, U. Fetzer, C. Steinbrueckner, Angew. Chem. 1959, 71, 386.
3. O. Kappe, Acc. Chem. Res. 2000, 33, 879.
4. A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300; Angew. Chem. Int. Ed. 2000, 39, 3168.
5. R. V. A. Orru, M. de Greef, Synthesis 2003, 1471.
6. T. Ngouansavanh, J. Zhu, Angew. Chem. 2006, 118, 3575; Angew. Chem. Int. Ed. 2006, 45, 3495.
7. A. Dömling, Chem. Rev. 2006, 106, 17.
8. D. Tejedor, F. Garcia-Tellado, Chem. Soc. Rev. 2007, 36, 484.
9. M. Somei, F. Yamada, Nat. Prod. Rep. 2005, 22, 73.
10. A. C. Kinsman, M. A. Kerr, J. Am. Chem. Soc. 2003, 125, 14120.
11. F. J. Chang, J. B. Rangisetty, M. Dukat, V. Setola, T. Raffay, B. Roth, R. A. Glennon, Bioorg. Med. Chem. Lett. 2004, 14, 1961.
12. K. Diker, M. Döé de Maindreville, D. Royer, F. Le Provost, J. Lévy, Tetrahedron Lett. 1999, 40, 7463.
13. G. W. Zhang, L. Wang, J. Nie, J. A. Ma, Adv. Synth. Catal. 2008, 350, 1457.
14. P. Galzerano, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 8032; Angew. Chem. Int. Ed. 2009, 48, 7892.
15. S. Shirakawa, S. Kobayashi, Org. Lett. 2006, 8, 4939.
16. Y. Qu, F. Ke, L. Zhou, Z. Li, H. Xiang, D. Wua, X. Zhou, Chem. Commun. 2011, 47, 3912.
17. A. Decortes, M. Martínez Belmonte, J. Benet-Buchholz, A. W. Kleij, Chem. Commun. 2010, 46, 4580.
18. A. Decortes, A. W. Kleij, ChemCatChem 2011, 3, 831.
19. A. W. Kleij, Dalton Trans. 2009, 4635.
20. A. W. Kleij, Chem. Eur. J. 2008, 14, 10520.
21. E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Chem. Eur. J. 2009, 15, 4233.
22. S. J. Wezenberg, G. Salassa, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Angew. Chem. Int. Ed. 2011, 50, 713.
23. E. Delahaye, M. Diop, R. Welter, M. Boero, C. Massobrio, P. Rabu, G. Rogez, Eur. J. Inorg. Chem. 2010, 4450.
24. A. Dalla Cort, L. Mandolini, C. Pasquini, K. Rissanen, L. Russo, L. Schiaffino, New J. Chem. 2007, 31, 1633.
25. 4 structure. See, for instance
26. T. Ohshima, T. Iwasaki, Y. Maegawa, A. Yoshiyama, K. Mashima, J. Am. Chem. Soc. 2008, 130, 2944.
27. T. Ohshima, T. Iwasaki, K. Mashima, Chem. Commun. 2006, 2711.
28. C. Jiao, M. Zhen, Y. Chao-Guo, Chem. Res. Chin. Univ. 2010, 26, 937.
29. We recently reported a versatile procedure for the in situ transmetalation of Zn(salphen) complexes, see:, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Inorg. Chem. 2007, 46, 7265.
30. C. Yue, A. Mao, Y. Wei, M. Lu, Catal. Commun. 2008, 9, 1571.
31. U. R. Pratap, D. V. Jawale, R. A. Waghmare, D. L. Lingampalle, R. A. Mane, New J. Chem. 2011, 35, 49.
32. A. W. Kleij, D. M. Tooke, M. Kuil, M. Lutz, A. L. Spek, J. N. H. Reek, Chem. Eur. J. 2005, 11, 4743.
33. G. M. Sheldrick, SHELXTL Crystallographic System, version 5.10, Bruker AXS, Inc., Madison, Wisconsin, 1998.