Photochemical reactions of 5-fluoropyrimidine bases with alcohols

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3243-3246

  Urjasz, Wojciech ^a   Maciejewski, Andrzej ^a   Celewicz, Lech ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

5 ALKOXYCYTOSINE; 6 ALKOXYCYTOSINE; ALCOHOL; DIHYDROFLUOROURACIL DERIVATIVE; FLUCYTOSINE; FLUOROPYRIMIDINE DERIVATIVE; FLUOROURACIL; UNCLASSIFIED DRUG;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOTOCHEMISTRY; PHOTOREACTIVITY; REACTION ANALYSIS; ULTRAVIOLET RADIATION;

EID: 0033574455     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00374-3     Document Type: Article

References (14)

1. Meisenheimer, K. M.; Koch, T. H. Crit. Rev. Biochem. Mol. Biol., 1997, 32, 101-140.
2. Shetlar, M. D. The Spectrum, 1994, 7, 12-19.
3. Norris, C. L.; Meisenheimer, K. M.; Koch, T. H. Photochem. Photobiol., 1997, 65, 201-207.
4. 18 reverse phase column (10 × 250 mm, 5 μm) using 5 mM aqueous lithium chloride as eluent. It was also possible to isolate the products by silica gel column chromatography using chloroform-methanol (50: 1 v/v) as eluent. In the case of photoreaction of 5-fluorocytosine with methanol the products 4, 5a and 6a were isolated in yields 9, 31 and 36%, respectively.
5. 18 reverse phase column (4.6 × 250 mm, 5 μm) using 2 mM aqueous lithium chloride as eluent.
6. max 2 = 243 nm (in 2mM aqueous lithium chloride).
7. +) 174 m/z.
8. 3), 122.2 (s, C-5), 132.9 (d, C-6), 158.2 (s, C-2), 162.2 (s, C-4).
9. Shaw, A. A.; Shetlar, M. D. Photochem. Photobiol., 1989, 49, 267-271.
10. Celewicz, L.; Shetlar, M. D. Photochem. Photobiol., 1992, 55, 823-830.
11. Robins, M. J.; MacCoss, M.; Naik, S. R.; Ramanii, G. J. Am. Chem. Soc., 1976, 98, 7381-7389.
12. Kobayasi, Y.; Kumadaki, I.; Nakazato, A. Tetrahedron Lett., 1980, 21, 4605-4606.
13. Visser, G. W. M.; Wedzinga, R.; Klok, R. P.; Herscheid, J. D. M. J. Chem. Soc., Perkin Trans. 2, 1994, 231-236.
14. Swanson, B. J.; Kutzer, J. C.; Koch, T. H. J. Am. Chem. Soc., 1981, 103, 1274-1276.