Photochemical ring expansion of 4-azidouracil: A route to 5H-1,3,5-triazepin-2,4-dione in the nucleoside series

Journal of Organic Chemistry

Volumn 71, Issue 4, 2006, Pages 1742-1745

  Peyrane, Frédéric ^a   Cesario, Michèle ^a   Clivio, Pascale ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOCHEMICAL BEHAVIOR; RING CONTRACTION;

NITROGEN; PHOTOCHEMICAL REACTIONS; STRUCTURE (COMPOSITION); X RAY CRYSTALLOGRAPHY;

KETONES;

2 AZIDOPYRIDINE; 2 OXOIMIDAZOLONE NUCLEOSIDE; 4 AZIDOURACIL; 5H 1,3,5 TRIAZEPIN 2,4 DIONE; AZEPINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PYRIDINE DERIVATIVE; TETRAZOLO[1,5 A]PYRIDINE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PHOTOCHEMISTRY; PHOTOLYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

AZEPINES; AZIDES; CARBODIIMIDES; NUCLEOSIDES; PHOTOCHEMISTRY; PYRIDINES; SOLVENTS; URACIL; WATER;

EID: 33644535774     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0524066     Document Type: Article

References (25)

1. (a) Hosmane, R. S. Curr. Top. Med. Chem. 2002, 2, 1093-1109.
2. (b) Hosmane, R. S.; Sood, R. K. Preparation of ring-expanded nucleosides and nucleotides as virucides and bactericides. United States Patent US 6677310, 2004.
3. (a) Liu, P. S.; Marquez, V. E.; Kelley, J. A.; Driscoll, J. S. J. Org. Chem. 1980, 45, 5225-5227.
4. (b) Marquez, V. E.; Liu, P. S.; Kelley, J. A.; Driscoll, J. S.; McCormack, J. J. J. Med. Chem. 1980, 23, 713-717.
5. (c) Marquez, V. E.; Liu, P. S.; Driscoll, J. S. Seven-Membered Ring Compounds as Inhibitors of Cytidine Deaminase. United States Patent US 4275057, 1981.
6. (d) Liu, P. S.; Marquez, V. E.; Driscoll, J. S.; Fuller, R. W. J. Med. Chem. 1981, 24, 662-666.
7. (e) Laliberté, J.; Marquez, V. E.; Momparler, R. L. Cancer Chemother. Pharmacol. 1992, 30, 7-11.
8. (f) Cristalli, G.; Volpini, R.; Vittori, S.; Camaioni, E.; Rafaiani, G.; Potenza, S.; Vita, A. Nucleosides Nucleotides 1996, 15, 1567-1580.
9. (a) Sawanishi, H.; Tsuchiya, T. J. Chem. Soc., Chem. Commun. 1990, 723-724.
10. (b) Reisinger, A.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1996, 813-814.
11. (c) Reisinger, A.; Koch, R.; Wentrup, C. J. Chem. Soc., Perkin Trans. 1 1998, 2247-2249.
12. (d) Reisinger, A.; Bernhardt, P. V.; Wentrup, C. Org. Biomol. Chem. 2004, 2, 246-256.
13. (e) Reisinger, A.; Koch, R.; Bernhardt, P. V.; Wentrup, C. Org. Biomol. Chem. 2004, 2, 1227-1238.
14. (a) Matsuda, A.; Obi, K.; Miyasaka, T. Chem. Pharm. Bull. 1985, 33, 2575-2578.
15. (b) De Napoli, L.; Mayol, L.; Piccialli, G.; Rossi, M.; Santacroce, C. J. Heterocycl. Chem. 1986, 23, 1401-1403.
16. (c) De Napoli, L.; Messere, A.; Montesarchio, D.; Piccialli, G.; Santacroce, C. Nucleosides Nucleotides 1991, 10, 1719-1728.
17. (d) Ciszewski, K.; Celewicz, L.; Golankiewicz, K. Biochem. Biophys. Res. Commun. 1992, 187, 1545-1550.
18. (e) Ciszewski, K.; Celewicz, L.; Golankiewicz, K. Synthesis 1995, 777-779.
19. (f) Kotra, L. P.; Wang, P.; Bartlett, M.; Shanmuganathan, K.; Xu, Z.; Cavalcanti, S.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1997, 62, 7267-7271.
20. (g) Mansour, T. S.; Evans, C. A.; Siddiqui, M. A.; Charron, M.; Zacharie, B.; Nguyen-Ba, N.; Lee, N.; Korba, B. Nucleosides Nucleotides 1997, 16, 993-1001.
21. Pyrex-filtered light emitted by a 150 W high-pressure Hg lamp.
22. Based on recovered starting material.
23. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205-8212.
24. Evans, R. A.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 4009-4017.
25. For a precedent example of photoreduction of the azide group in the presence of an amine, see: Miyasaka, T.; Tanaka, H.; Satoh, K.; Imahashi, M.; Yamaguchi, K. J. Heterocycl. Chem. 1987, 24, 873-875.