An efficient direct amination of cyclic amides and cyclic ureas

Organic Letters

Volumn 8, Issue 11, 2006, Pages 2425-2428

  Wan, Zhao Kui ^a   Wacharasindhu, Sumrit ^b   Binnun, Eva ^a   Mansour, Tarek ^b  

^a PFIZER INC   (United States)

^b WYETH RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMIDINE; GUANIDINE DERIVATIVE; KINETIN; OLOMOUCINE; UREA;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMIDES; AMIDINES; AMINATION; CATALYSIS; GUANIDINES; KINETIN; MOLECULAR STRUCTURE; UREA;

EID: 33745725794     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060815y     Document Type: Article

References (27)

1. Pozharskii, A. F.; Soldartenkov, A. T.; Katrizky, A. R. Heterocycles in Life and Society; Hohn Wiley & Sons: Weinheim, Germany, 1997.
2. (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
3. (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
4. (a) Wan, Z.-K.; Binnun, E.; Wilson, D. P.; Lee, J. Org. Lett. 2005, 7, 5877.
5. For the syntheses under optimized Opeal conditions, see: (b) Lin, X.; Robins, M. J. Org. Lett. 2000, 2, 3497.
6. (c) Véliz, E. A.; Beal, P. A. J. Org. Chem. 2001, 66, 8592.
7. For representative recent reviews, see: (a) Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W, R.; Connors R. W.; Bridges, A. J. Science 1994, 265, 1093.
8. (b) Bridges, A. J. Chem. Rev. 2001, 101, 2541.
9. For a recent synthesis, see: Yoon, D. S.; Han, Y.; Stark, T. M.; Haber J. C.; Gregg, B. T.; Stankovich, S. B. Org. Lett. 2004, 6, 4775.
10. PyBOP and PyBrOP were found to be less efficient (data not shown).
11. 2 column.
12. Yields given after purification, unless otherwise noted.
13. 31P NMR studies. The phosphoninum salt A could also be detected occasionally.
14. Mechanistic studies and applications of these synthetic intermediates are underway. For work on BtH, see: Katritzky, R. A.; Manju, K.; Singh, S. K.; Meher, N. K. Tetrahedron 2005, 61, 2555.
15. At room temperature, reactions of 5a with anilline did not proceed while a small amount of 5f was observed within a few minutes by LCMS analysis in the reaction conditions listed in entry 6, Table 3.
16. Peng, Z.-H.; Journet, M.; Humphrey, G. Org. Lett. 2006, 8, 395.
17. Isolation: (a) Miller, C. O.; Skoog, F.; Von Saltza, M. H.; Strong, F. M. J. Am. Chem. Soc. 1955, 77, 1392.
18. (b) Miller, C. O.; Skoog, F.; Okumura, F. S.; Von Saltza, M. H.; Strong, F. M. J. Am. Chem. Soc. 1956, 78, 1375.
19. For syntheses see ref 13b and: (c) Villar, J. D. F.; Motta, M. A. Nucleosides, Nucleotides & Nucleic Acids 2000, 19, 1005.
20. Barciszewski, J.; Mielcarek, M.; Stobiecki, M.; Siboska, G.; Clark, B. F. C. Biochem. Biophys. Res. Commun. 2000, 279, 69.
21. For a recent review on kinetin see: Barciszewski, J.; Rattan, S. I. S.; Siboska, G.; Clark, B. F. C. Plant Sci. 1999, 148, 37.
22. For representative biological activities see: (a) Vesely, J.; Havlicek, L.: Strnad, M.; Blow, J.; Donella-Deana, A.; Pinna, L.; Letham, D.; Kato, J.; Detivaud, L.; Leclerc, S.; Meijer, L. Eur. J. Biochem. 1994, 224, 771.
23. (b) Mistelli, T.; Warren, G. J. Cell Sci. 1995, 108, 2715.
24. (c) Hartwell, L. H.; Kastan, M. B. Science 1994, 266, 1821.
25. For recent 6-9 step syntheses see: (d) Nugiel, D. A.; Cornelius, L. A. M.; Corbett, J. W. J. Org. Chem. 1997, 62, 201.
26. (e) Dorff, P. H.; Garigipati, R. S. Tetrahedron Lett. 2001, 42, 2771.
27. (f) Hammarström, L. G. J.; Smith, D. B.; Talamás, F. X.; Labadie, S. S.; Krauss, N. E. Tetrahedron Lett. 2002, 43, 8071.