Simple, versatile, and efficient catalysts for guanylation of amines

Organometallics

Volumn 29, Issue 12, 2010, Pages 2789-2795

  Alonso Moreno, Carlos ^a   Carrillo Hermosilla, Fernando ^a   Garcés, Andrés ^b   Otero, Antonio ^a   López Solera, Isabel ^a   Rodríguez, Ana M ^a   Antiñolo, Antonio ^a  

^a Analytical Chemistry and Food Science Dept   (Spain)

^b UNIVERSIDAD REY JUAN CARLOS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDO COMPOUNDS; AROMATIC PRIMARY AMINES; CARBODIIMIDES; CATALYTIC ADDITION; CATALYTIC PRECURSORS; EFFICIENT CATALYSTS; GUANIDINATES; GUANYLATION; HETEROCYCLIC AMINES; INSERTION PROCESS; SECONDARY AMINES; STRUCTURAL CHARACTERIZATION; SYNTHESIS AND CHARACTERIZATION;

AMINES; CATALYSTS; LITHIUM; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL); ZINC;

COMPLEXATION;

EID: 77953747935     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1003122     Document Type: Article

References (33)

1. Berlinck, R. G. S.; Burtoloso, A. C. B.; Kossuga, M. H. Nat. Prod. Rep. 2008, 25, 919
2. Durant, G. J. Chem. Soc. Rev. 1985, 14, 375
3. The Pharmacological Basis of Therapeutics, 7 th ed.; Gilman, A.; Gododman, L. S.; Rall, T. W.; Murad, T., Eds.; Pergamon Press: New York, 1990; p 899.
4. Coles, M. P. Dalton Trans. 2006, 985
5. See for example: Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133
6. Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553
7. Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161
8. Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038
9. Thomas, E. W.; Nishizawa, E. E.; Zimmermann, D. C.; Williams, D. J. J. Med. Chem. 1989, 32, 228
10. Zhang, W.-X.; Hou, Z. Org. Biomol. Chem. 2008, 6, 1720
11. Schow, S. In Encyclopedia of Reagents for Organic Synthesis; Paquete, L. A., Ed.; Wiley: Sussex, U.K., 1995; pp 1408-1410.
12. Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 8100
13. Ong, T.-G.; OBrien, J. S.; Korobkov, I.; Richeson, D. S. Organometallics 2006, 25, 4728
14. Zhang, W.-X.; Nishiura, M.; Hou, Z. Synlett 2006, 8, 1213
15. Zhang, W.-X.; Nishiura, M.; Hou, Z. Chem.- Eur. J. 2007, 13, 4037
16. Zhou, S.; Wang, S.; Yang, G.; Li, Q.; Zhang, L.; Yao, Z.; Zhou, Z.; Song, H. Organometallics 2007, 26, 3755
17. Li, Q.; Wang, S; Zhou, S.; Yang, G.; Zhu, X.; Liu, Y. J. Org. Chem. 2007, 72, 6763
18. Wu, Y.; Wang, S.; Zhang, L.; Yang, G.; Zhu, X.; Liu, C.; Yin, C.; Rong, J. Inorg. Chim. Acta 2009, 2814
19. Shen, H.; Chan, H. S.; Xie, Z. Organometallics 2006, 25, 5515
20. Montilla, F.; Pastor, A.; Galindo, A. J. Organomet. Chem. 2004, 689, 993
21. Zhang, W.-X.; Li, D.; Wang, Z.; Xi, Z. Organometallics 2009, 28, 882
22. 2, as an effective catalyst for guanylation reactions were reported: Li, D.; Guang, J.; Zhang, W.-X.; Wang, Y.; Xi, Z. Org. Biomol. Chem. 2010, DOI: 10.1039/b923249b.
23. Lachs, J. R.; Barret, A. G. M.; Crimmin, M. R.; Kociock-Kohn, G.; Hill, M. S.; Mahon, M. F.; Procopiou, P. A. Eur. J. Inorg. Chem. 2008, 4173
24. Alonso-Moreno, C.; Carrillo-Hermosilla, F.; Romero-Fernández, J.; Rodríguez, A. M.; Otero, A.; Antiñolo, A. Adv. Synth. Catal. 2009, 351, 881
25. Otero, A.; Fernandez-Baeza, J.; Lara-Sanchez, A.; Alonso-Moreno, C.; Marquez-Segovia, M. I.; Sanchez-Barba Merlo, L. F.; Rodriguez, A. M. Angew. Chem. 2009, 48, 2176
26. Otero, A.; Fernandez-Baeza, J.; Antiñolo, A.; Lara-Sanchez, A.; Tejeda, J.; Martinez-Caballero, E.; Marquez-Segovia, I.; Lopez-Solera, I.; Sanchez-Barba Merlo, L. F.; Alonso-Moreno, C. Inorg. Chem. 2008, 47, 4996
27. Otero, A.; Fernandez-Baeza, J.; Lara-Sanchez, A.; Martinez-Caballero, E.; Tejeda, J.; Sanchez-Barba Merlo, L. F.; Antiñolo, A.; Alonso-Moreno, C.; Lopez-Solera, I. Organometallics 2008, 27, 976
28. Alonso-Moreno, C.; Garces Osado, A.; Sanchez-Barba Merlo, L. F.; Fernandez-Baeza, J.; Otero, A.; Lara-Sanchez, A.; Antiñolo, A.; Broomfield, L.; Lopez-Solera, I. Organometallics 2008, 27, 1310
29. Sánchez-Barba, L. F.; Garcés, A.; Fajardo, M.; Alonso-Moreno, C.; Otero, A.; Fernández-Baeza, J.; Antiñolo, A.; Tejeda, J.; Lara-Sánchez, A.; López-Solera, I. Organometallics 2007, 26, 6403
30. Coles, M. P.; Hitchcock, P. B. Eur. J. Inorg. Chem. 2004, 2662
31. SAINT+ v7.12a, Area-Detector Integration Program; Bruker-Nonius AXS: Madison, WI, 2004.
32. Sheldrick, G. M. SADABS version 2004/1, A Program for Empirical Absorption Correction; University of Göttingen: Göttingen, Germany, 2004.
33. SHELXTL-NT version 6.12, Structure Determination Package; Bruker-Nonius AXS: Madison, WI, 2001.