Formation of benzooxaphosphole oxide heterocyclic system by the ring-contractive Arbuzov-Michaelis isomerization of alkoxy-substituted benzodioxaphosphorins

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 177, Issue 1, 2002, Pages 251-259

  Nifantiev, Eduard E ^a   Khrebtova, Svetlana B ^a   Kulikova, Yulia V ^a   Predvoditelv, Dmitrii A ^a   Kukhareva, Tat'yana S ^b   Petrovskii, Pavel V ^c   Rose, Mirjam ^c   Meier, Chris ^c  

^a MOSCOW STATE PEDAGOGICAL UNIVERSITY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c UNIVERSITY OF HAMBURG   (Germany)

Author keywords

2 hydroxybenzylic alcohol; Arbuzov Michaelis type isomerization; Benzodioxaphosphorins; Benzooxaphosphole oxides; Cyclosaligenyl nucleotides; Saligenin

Indexed keywords

BENZODIOXAN DERIVATIVE; BENZOOXAPHOSPHOLE OXIDE; HETEROCYCLIC COMPOUND; NUCLEOSIDE; PHOSPHOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARBUZOV REACTION; ARTICLE; ATOM; CARBON NUCLEAR MAGNETIC RESONANCE; ISOMERISM; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0036032419     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500210234     Document Type: Article

References (43)

1. A. B. Ageeva and B. E. Ivanov, Izv. Akad. Nauk, Ser. Khim., 1494 (1967). (Bull. Acad. Sci. USSR, Div. Chem. Sci., 16, 1443 (1967).
2. A. B. Ageeva and B. E. Ivanov, Izv. Akad. Nauk, Ser. Khim., 1494 (1967). (Bull. Acad. Sci. USSR, Div. Chem. Sci., 16, 1443 (1967).
3. B. E. Ivanov, A. B. Ageeva, A. G. Abul'khanov, and T. A. Zyablikova, Izv. Akad. Nauk. Set. Khim., 1912 (1969).
4. W. Vogt, Phosphorus, and Sulfur, 5, 123 (1978).
5. D. W. Chaser, J. Org. Chem., 48, 4768 (1983).
6. E. E. Nifantiev and A. I. Zavalishina, Usp. Khim., 51, 1601 (1982).
7. E. E. Nifantiev, T. S. Kukhareva, V. I. Dyachenko, A. O. Kolomietz, N. S. Magomedova, V. K. Belsky, and L. K. Vasyanina, Phosphorus, Sulfur, and Silicon, 92, 29 (1994).
8. A. Wissner, M. L. Carroll, K. E. Green, S. S. Kerwar, W. C. Pickett, R. E. Schaub, L. W. Torley, S. Wrenn, and C. A. Kohler, J. Med. Chem., 35, 1650 (1992).
9. C. Meier, E. De Clercq, and J. Balzarini, Eur. J. Org. Chem., 837 (1998).
10. Methoden der Organischen Chemie (Houben-Weyl), XII/1, S. 433 (1963). XII/2, S. 80 (1964). E2, 380 (1982).
11. Methoden der Organischen Chemie (Houben-Weyl), XII/1, S. 433 (1963). XII/2, S. 80 (1964). E2, 380 (1982).
12. Methoden der Organischen Chemie (Houben-Weyl), XII/1, S. 433 (1963). XII/2, S. 80 (1964). E2, 380 (1982).
13. F. Cramer and D. Voges, Chem. Ber., 92, 952 (1959).
14. N. I. Rizpolozhensky and F. S. Mukhametov, Izv. Akad. Nauk, Ser. Khim., 2163 (1968). Bull. Acad. Sci. USSR, Div. Chem. Sci., 17, 2058 (1968).
15. N. I. Rizpolozhensky and F. S. Mukhametov, Izv. Akad. Nauk, Ser. Khim., 2163 (1968). Bull. Acad. Sci. USSR, Div. Chem. Sci., 17, 2058 (1968).
16. A. N. Pudovik and I. M. Aladzheva, J. Gen. Chem. USSR, 33, 3022 (1963).
17. V. Mark, Mechanisms of Molecular Migration, (New York, 1969), chap. 2, p. 319.
18. F. Mathey and D. Thavard, J. Organometal. Chem., 117, 377 (1976).
19. H.-D. Block and H. Dahmen, EP 43482 (1981/82). Bayer A. G. Chem. Abstr., 96, 199879d (1982).
20. H.-D. Block and H. Dahmen, EP 43482 (1981/82). Bayer A. G. Chem. Abstr., 96, 199879d (1982).
21. J. Omelanzcuk, A. E. Sopchik, S.-G. Lee, K. Akutagawa, S. M. Cairns, and W. G. Bentrude, J. Am. Chem. Soc., 110, 6908 (1988).
22. K. B. Mullah and W. G. Bentrude, J. Org. Chem., 56, 7218 (1991).
23. W. Bhanthumnavin and W. G. Bentrude, J. Org. Chem., 66, 980 (2001).
24. Sh. Yasui, K. Shioji, M. Tsujimoto, and A. Ohno, Tetrahedron Lett., 37, 1625 (1996).
25. V. Mark, Tetrahedron Lett., 281 (1962).
26. A. P. Boisselle and N. A. Meinhardt, J. Org. Chem., 27, 1828 (1962).
27. A. N. Pudovik, I. M. Aladzheva, and L. N. Yakovenko, J. Gen. Chem., 35, 1210 (1965).
28. N. M. Ivakina, Yu. A. Kondrat'ev, and S. Z. Ivin, J. Gen. Chem., 37, 1691 (1967).
29. A. Sevin and W. Chodkiewiecz, Bull. Soc. Chem. Fr., 4016 (1969).
30. E. E. Nifantiev, M. K. Gratchev, and S. Yu. Burmistrov, Chem. Rev., 100, 3755 (2000).
31. C. Meier, Angew. Chem. Int. Ed., 35, 70 (1996).
32. C. Meier, M. Lorey, E. De Clercq, and J. Balzarini, Bioorg. Med. Chem. Lett., 7, 99 (1997).
33. C. Meier, T. Knispel, E. De Clercq, and J. Balzarini, Bioorg. Med. Chem. Lett., 7, 1577 (1997).
34. M. Lorey, C. Meier, E. De Clercq, and J. Balzarini, Nucleos. Nucleot., 16, 789 (1997).
35. C. Meier, E. De Clercq, and J. Balzarini, Nucleos. Nucleot., 16, 793 (1997).
36. C. Meier, M. Lorey, E. De Clercq, and J. Balzarini, Nucleos. Nucleot., 16, 1303 (1997).
37. M. Lorey, C. Meier, E. De Clercq, and J. Balzarini, Nucleos. Nucleot., 16, 1307 (1997).
38. C. Meier, Synlett., 233 (1998).
39. C. Meier, M. Lorey, E. De Clercq, and J. Balzarini, J. Med. Chem., 41, 1417 (1998).
40. C. Meier, L. Habel, F. Haller-Meier, A. Lomp, M. Herderich, R. Klöcking, A. Meerbach, and P. Wutzler, Antiviral Chem. Chemother., 9, 389 (1998).
41. C. Meier, T. Knispel, E. DeClercq, and J. Balzarini, J. Med. Chem., 42, 1604 (1999).
42. C. Meier, T. Knispel, V. E. Marquez, M. A. Siddiqui, E. DeClercq, and J. Balzarini, J. Med. Chem., 42, 1615 (1999).
43. C. Meier, A. Lomp, A. Meerbach, and P. Wutzler, Chem. Bio. Chem., 2, 283 (2001).