3-(Arylamino)-1,2,4-triazin-5-one: A novel synthesis and its use

European Journal of Organic Chemistry

Volumn , Issue 15, 2010, Pages 2852-2854

  Leenders, Ruben ^a   Heeres, Jan ^b   Vandenput, Dirk ^a   Zijlmans, Remco ^a   Guillemont, Jérôme ^c   Lewi, Paul ^b  

^a Mercachem BV   (Netherlands)

^b JANSSEN RESEARCH FOUNDATION   (Belgium)

^c JOHNSON AND JOHNSON   (United States)

Author keywords

Antiviral agents; Medicinal chemistry; Nitrogen heterocycles

Indexed keywords

EID: 77952182686     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000242     Document Type: Article

References (13)

1. Some of the compounds in this paper were claimed in: P. J. Lewi, P. A. J. Janssen, M. R. de Jonge, L. M. H. Koymans, H. M. Vinkers, F. F. D. Daeyaert, J. Heeres, R. G. G. Leenders, G. J. C. Hoornaert, A. Kilonda, D. W. Ludovici, WO2004/ 074266, 2004.
2. This hydroxy function can be functionalized after chlorination, triflation, mesylation etc. with or without palladium catalysis; alkylated; used in the Mitsunobu reaction etc.
3. [1]
4. a) T. Ueda, M. Furukawa, Chem. Pharm. Bull. 1964, 12, 100-103;
5. b) A. K. Mansour, S. B. Awad, S. Antoun, Z. Naturforsch., Teil B 1974, 29, 792-796;
6. c) A. K. Mansour, Y. A. Ibrahim, J. Prakt. Chem. (Leipzig) 1973, 315, 221-226.
7. R.-Y. Yang, A. P. Kaplan, Tetrahedron Lett. 2001, 42, 4433-4435.
8. See: R. Leenders, J. Heeres, J. Guillemont, P. Lewi, Tetrahedron Lett. 2010, 51, 543-544 and the literature cited there under references [1] and [2].
9. G. J. C. Hoornaert, A. Kilonda, J. Heeres, P. J. Lewi, M. R. de Jonge, F. F. D. Daeyaert, H. M. Vinkers, L. M. H. Koymans, P. A. J. Janssen, WO2006015985, 2006.
10. P. J. Lewi, M. R. de Jonge, L. M. H. Koymans, F. F. D. Daeyaert, J. Heeres, H. M. Vinkers, R. G. G. Leenders, D. A. L. Vandenput, WO 2005/028479, 2005.
11. 2CN.
12. D. W. Ludovici, M. J. Kukla, P. G. Grous, S. Krishnan, K. Andries, M.-P. de Béthune, H. Azijn, R. Pauwels, E. de Clercq, E. Arnold, P. A. J. Janssen, Bioorg. Med Chem. Lett. 2001, 11, 2225-2228.
13. These compounds have a very adverse solubility making column chromatography impossible.