Controlled C-5 chlorination and dichlorohydrin formation of uracil ring with HCl/DMF/Oxone® system

Bulletin of the Korean Chemical Society

Volumn 33, Issue 4, 2012, Pages 1357-1359

  Lee, Hyun Seung ^a   Lee, Hyun Ju ^a   Lee, Ka Young ^b   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

^b National Forensic Service   (South Korea)

Author keywords

Chlorination; Dichlorohydrin; DMF; HCl; Oxone

Indexed keywords

EID: 84860109414     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2012.33.4.1357     Document Type: Article

References (22)

1. Ryu, E. K.; MacCoss, M. J. Org. Chem. 1981, 46, 2819-2823.
2. For the chlorination of nucleic acid bases with benzoyl chloride, see: Ryu, E. K.; Kim, J. N. Nucleosides & Nucleotides 1989, 8, 43-48.
3. For the iodination of uracil derivatives, see: Hwang, C. H.; Park, J. S.; Won, J. H.; Kim, J. N.; Ryu, E. K. Arch. Pharm. Res. 1992, 15, 69-72.
4. For the chlorination with HCl/DMF/Oxone® system, see: (a) Kim, J. N.; Ryu, E. K. J. Org. Chem. 1992, 57, 6649-6650.
5. (b) Kim, J. N.; Son, J. S.; Lee, H. J.; Jung, K. S. Synth. Commun. 1997, 27, 1885-1891.
6. (c) Kim, K. K.; Kim, J. N.; Kim, K. M.; Kim, H. R.; Ryu, E. K. Chem. Lett. 1992, 603-604.
7. For the chlorination with HCl/DMF/m-CPBA system, see: (a) Chung, K. H.; Kim, H. J.; Kim, H. R.; Ryu, E. K. Synth. Commun. 1990, 20, 2991-2997.
8. (b) Chung, K. H.; Kim, K. M.; Kim, J. N. Ryu, E. K. Synth. Commun. 1991, 21, 1917-1922.
9. (c) Kim, H. J.; Kim, H. R.; Kim, J. N.; Ryu, E. K. Bull. Korean Chem. Soc. 1990, 11, 184-186.
10. (d) Kim, K. M.; Chung, K. H.; Kim, J. N.; Ryu, E. K. Synthesis 1993, 283-284.
11. Lee, H. S.; Kim, K. H.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2012, 53, 497-501.
12. 6 compound 2a was prepared in 70% by the literature method involving the use of LiCl/CAN, see: Asakura, J.; Robins, M. J. J. Org. Chem. 1990, 55, 4928-4933.
13. (a) Itahara, T.; Ebihara, R.; Fujii, Y.; Tada, M. Chem. Lett. 1986, 1319-1322.
14. (b) Itahara, T. Chem. Lett. 1987, 841-844.
15. For the synthesis of 1,3-dimethyl-6-phenyluracil, see: Kim, K. H.; Lee, H. S.; Kim, J. N. Tetrahedron Lett. 2011, 52, 6228-6233.
16. For the reaction of uracil derivatives with hypochlorous acid and related species, see: (a) Hoyano, Y.; Bacon, V.; Summons, R. E.; Pereira, W. E.; Halpern, B.; Duffield, A. M. Biochem. Biophys. Res. Comm. 1973, 53, 1195-1199.
17. (b) Tee, O. S.; Banerjee, S. Can. J. Chem. 1979, 57, 626-634.
18. For our contributions on chloroformyloxylation and related reactions, see: (a) Son, J. S.; Jung, K. S.; Kim, H. R.; Kim, J. N. Synth. Commun. 1998, 28, 1847-1855.
19. (b) Kim, H. R.; Oh, H. S.; Park, H. J.; Kim, J. N.; Jeon, D. J.; Ryu, E. K. Synth. Commun. 1998, 28, 159-165.
20. (c) Kim, J. N.; Son, J. S.; Kim, H. R.; Ryu, E. K. Bull. Korean Chem. Soc. 1998, 19, 812-813.
21. (a) Senda, S.; Hirota, K.; Banno, K. J. Med. Chem. 1972, 15, 471-476.
22. (b) Wang, S. Y. J. Org. Chem. 1959, 24, 11-13.