Synthesis of pyrazine-phosphonates and -phosphine oxides from 2H-azirines or oximes

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2405-2408

  Palacios, Francisco ^a   Ochoa De Retana, Ana María ^a   Gil, José Ignacio ^a   López De Munain, Rafael ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRINE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OXIME; PHOSPHONIC ACID DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; SYNTHESIS;

AZIRINES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OXIMES; PHOSPHONIC ACIDS; PHOSPHORYLATION; PYRAZINES;

EID: 0037062860     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0261534     Document Type: Article

References (41)

1. For recent reviews on pyrazines see: (a) McCullough, K. L. In Heterocyclic Compounds. Rodd's Chemistry of Carbon Compounds, 2nd ed., 2nd supplement; Sainsbury, M., Ed.; Elsevier: Amsterdam, 2000; Vol. 4, Parts I-J, pp 99-171.
2. (b) Urban, S.; Hickford, S. J. H.; Blunt, J. W.; Munro, M. H. G. Curr. Org. Chem. 2000, 4, 765.
3. Ohta, A.; Aoyagi, Y. Rev. Heteroat. Chem. 1998, 18, 141.
4. Sato, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Boulton, A. J., Eds.; Elsevier: Oxford, 1996; Vol. 6, pp 233-278.
5. For recent contributions see: (a) Gohlke, H.; Gundisch, D.; Schwarz, S.; Seitz, G.; Tilotta, M. C.; Wegge, T. J. Med. Chem. 2002, 45, 1065.
6. (b) Ragnarsson, U.; Grehn, L.; Maia, H. L.; Monteiro, L. S. Org. Lett. 2001, 3, 2021.
7. Liu, W.; Wise, D. S.; Townsend, L. B. J. Org. Chem. 2001, 66, 4783.
8. Cavalier, J. F.; Burton, M.; Dussart, F.; Marchand, F.; Rees, J. F.; Marchant-Brynaert, J. Bioorg. Med. Chem. 2001, 9, 1037.
9. (e) Shibata, K.; Fukuwatari, T.; Sugimoto, E. Biochemistry 2001, 65, 1339.
10. (a) LaCour, T. G.; Guo, C.; Boyd, M. R.; Fuchs, P. L. Org. Lett. 2000, 2, 33.
11. (b) Basler, S.; Brunck, A.; Jautelat, R.; Winterfeldt, E. Helv. Chim. Acta 2000, 83, 1854.
12. LaCour, T. G.; Guo, C.; Ma, S.; Jeong, J. U.; Boyd, M. R.; Matsunaga, S.; Fusetani, N.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1999, 9, 2587.
13. Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672.
14. (a) Suzuki, Y.; Suzuki, A.; Tamaru, A.; Katsukawa, C.; Oda, H. J. Clin. Microbiol. 2002, 40, 501.
15. (b) Zhang, Y.; Permar, S.; Sun, Z. J. Clin. Microbiol. 2002, 40, 42.
16. Bothamley, G. Drug Saf. 2001, 24, 553.
17. Zimhony, O.; Cox, J. S.; Welch, J. T.; Vilcheze, C.; Jacobs, W. R. Nat. Med. (NY) 2000, 6, 1043.
18. (a) Cynamon, M. H.; Speirs, R. J.; Welch, J. T. Antimicrob. Agents Chemother. 1998, 42, 462.
19. (b) Bergmann, K. E.; Cynamon, M. H.; Welch, J. T. J. Med. Chem. 1996, 39, 3394.
20. Speirs, R. J.; Welch, J. T.; Cynamon, M. H. Antimicrob. Agents Chemother. 1995, 39, 1269.
21. For reviews, see: (a) Engel, R. Handbook of Organophosphorus Chemistry; Marcel Dekker, Inc.: New York, 1992.
22. (b) Kafarski, P.; Lejczak, B. Phosphorus Sulfur 1991, 63, 193-215.
23. Toy, A. D. F.; Walsh, E. N. Phosphorus Chemistry in Everyday Living; American Chemical Society: Washington, DC, 1987; p 333.
24. For recent reviews on azirines, see: (a) Palacios, F.; Ochoa de Retana, A. M.; Martinez de Marigorta, E.; de los Santos, J. M. Org. Prep. Proced. Int. 2002, 34, 219-269.
25. (b) Gilchrist, T. L. Aldrichimica Acta 2001, 34, 51-55.
26. Palacios, F.; Ochoa de Retana, A. M.; Martinez de Marigorta, E.; de los Santos, J. M. Eur. J. Org. Chem. 2001, 2401-2414.
27. Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I.; Ezpeleta, J. M. J. Org. Chem. 2000, 65, 3213-3217.
28. Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I. Tetrahedron Lett. 2000, 41, 5363-5366.
29. The asymmetric synthesis of diethyl 2-phenyl-2H-azirine-3-phosphonate (62%) and the isomeric 3-phenyl-2H-azirine-2-phosphonate (15%) from chiral aziridines has been reported. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249-252.
30. The asymmetric synthesis of dimethyl 2-aryl-2H-azirine-3-phosphonates with a small proportion of the isomeric 3-aryl-2H-azirine-2-phosphonate by Swern oxidation of chiral cis-aziridine phosphonates and the use as a dienophile in cycloaddition reactions of 2H-azirine-3-phosphonates have been recently reported. Davis, F. A.; Wu, Y.; Yan, H.; Prasad, K. R.; McCoull, W. Org. Lett. 2002, 4, 655-658.
31. (a) Aurichio, S.; Grassi, S.; Malpezzi, L.; Sartori, A. S.; Truscello, A. M. Eur. J. Org. Chem 2001, 1183-1187.
32. (b) Alves, M. J.; Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1998, 299-303.
33. Hugener, M.; Heimgartner, H. Helv. Chim. Acta 1995, 78, 1490-1498.
34. Knittel, D. Synthesis 1985, 186-188.
35. (e) Alper, H.; Prickett, J. E.; Wollwitz, S. J. Am. Chem. Soc. 1977, 99, 4330-4333.
36. (f) Padwa, A. Acc. Chem. Res. 1976, 9, 371-378.
37. 2 atmosphere. The crude product was purified by chromatography using silica gel (hexane/ethyl acetate).
38. Chandrasekhar, S.; Gopalaiah, K. Tetrahedron Lett. 2001, 42, 8123-8125.
39. Smolinsky, G.; Pride, C. A. J. Org. Chem. 1968, 33, 2411-2416.
40. 2 atmosphere. The crude product was purified by chromatography using silica gel (hexane/ethyl acetate).
41. 4, and evaporated under vacuum. The crude product was purified by chromatography using silica gel (hexane/ethyl acetate).