An efficient strategy for the regioselective synthesis of 3- phosphorylated-1-aminopyrroles from β-hydrazono phosphine oxides and phosphonates

Tetrahedron

Volumn 55, Issue 48, 1999, Pages 13767-13778

  Palacios, Francisco ^a   Aparicio, Domitila ^a   De Los Santos, Jesús M ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HYDROLYSIS; PHOSPHORYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033607652     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00860-1     Document Type: Article

References (47)

1. 1. For excellent reviews see: a) Gribble, G. W. in "Comprehensive Heterocyclic Chemistry II", vol. 2, Chapt. 4. Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon-Elsevier, Amsterdam, 1996.
2. b) Sundberg, R. J. in "Comprehensive Heterocyclic Chemistry", vol. 4, pp. 314-376. Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press, Oxford, 1984.
3. 2. a) Goller, M. I.; Barthet, C.; McCarthy, G. P.; Corradi, R.; Newby, B. P.; Wilson, S. A.; Armes, S. P.; Luk, S. Y., Coll. Polym. Sci., 1998, 276, 1010.
4. b) Attanasi, O. A.; De Crescentini, L.; Foresti, E.; Gatti, G.; Giorgi, R.; Perrulli, F. R.; Santeusanio, S. J. Chem. Soc., Perkin Trans. 1, 1997, 1829.
5. c) Quintela, J. M.; Moreira, M. J.; Peinador, C. Tetrahedron, 1996, 52, 3037.
6. d) Jacobi, P. A.; Buddhu, S. C.; Fry, D.; Rajeswari, S. J. Org. Chem., 1997, 62, 2894.
7. e) Effland, R. C.; Klein, J. T. U. S. Patent 4,546,105, 1985. Chem. Abstr., 1986, 104, 186307.
8. f) Kulagowski, J.; Janusz, J.; Leeson, P. D. UK Patent 2,265,372, 1993. Chem. Abstr., 1993, 120, 134504.
9. g) Attanasi, O. A.; Colombani, S. M.; De Crescentini, L.; Giorgi, R.; Monti, S.; Perrone, A.; Perrulli, F. R.; Renzetti, A. R.; Santeusanio, S. Farmaco, 1999, 54, 64.
10. 3. For reviews see: a) Cirrincione, G.; Almerico, A. M.; Aiello, E. in "Pyrroles. The Chemistry of Heterocyclic Compounds"; Jones, R. A., Ed.; Wiley: New York, 1992; vol. 48, Pt. 2, Chapt. 3.
11. b) Bean, G. P. in "Pyrroles. The Chemistry of Heterocyclic Compounds"; Jones, R. A., Ed.; Wiley: New York, 1990; vol. 48, Pt. 1, Chapt. 2.
12. c) Jones, R. A.; Bean, G. P. in "The Chemistry of Pyrroles", Academic Press, London, 1977.
13. 4. For recent contributions see: a) Attanasi, O. A.; De Crescentini, L.; Fillippone, P.; Perrulli, F. R.; Santeusanio, S. Synlett, 1999, 339.
14. b) Jolivet Fouchet, S.; Hamelin, J.; Texier Boullet, F.; Toupet, L.; Jacquault, P. Tetrahedron, 1998, 54, 4561.
15. c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett, 1997, 1315.
16. d) McLeod, M.; Boudreault, N.; Leblanc, Y. J. Org. Chem., 1996, 61, 1180.
17. e) Seino, H.; Ishii, Y.; Sasagawa, T.; Hidai, M. J. Am. Chem. Soc., 1995, 117, 12181.
18. 5. Attanasi, O. A.; Fillippone, P.; Mei, A.; Bongini, A.; Foresti, E. Tetrahedron, 1990, 46, 4685.
19. 6. For excellent reviews in the use of conjugated aza-alkenes in organic synthesis see: a) Attanasi, O. A.; Filippone, P. Synlett, 1997, 1128.
20. b) Attanasi, O. A.; Filippone, F. in "Topics in Heterocyclic Systems-Synthesis, Reactions and Properties", Attanasi, O. A.; Spinelli, D. Eds.; 1996, vol. 1, p. 157.
21. c) Attanasi, O. A.; Filippone, P.; Serra-Zanetti, F. in "Progress in Heterocyclic Chemistry", Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon, Oxford, 1995, vol. 7, Chapt. 1, p. 1.
22. d) Attanasi, O. A.; Filippone, P.; Serra-Zanetti, F. in "Trends in Heterocyclic Chemistry", Menon, J. Ed.; 1993, vol. 3, p. 461.
23. 7. Toy, A. D. F.; Walsh, E. N. in "Phosphorus Chemistry in Everyday Living", American Chemical Society, Washington D. C., 1987. Engel, R. in "Handbook of Organophosphorus Chemistry", Dekker, M. Inc., New York, 1992.
24. 7. Toy, A. D. F.; Walsh, E. N. in "Phosphorus Chemistry in Everyday Living", American Chemical Society, Washington D. C., 1987. Engel, R. in "Handbook of Organophosphorus Chemistry", Dekker, M. Inc., New York, 1992.
25. 8. For recent contributions see: a) Palacios, F.; Ochoa de Retana, A.; Oyarzabal, J.; Ezpeleta, J. M. Tetrahedron, 1998, 54, 2281.
26. b) Palacios, F.; Pagalday, J.; Piquet, V.; Dahan, F.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1997, 61, 292.
27. c) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron, 1996, 52, 4123.
28. 9. a) Palacios, F.; Ochoa de Retana, A.; Oyarzabal, J. Tetrahedron, 1999, 55, 5947.
29. b) Palacios, F.; Aparicio, D.; Ochoa de Retana, A.; de los Santos, J. M.; García, J.; Oyarzabal, J. Tetrahedron, 1999, 55, 3105.
30. c) Palacios, F.; Aparicio, D.; García, J. Tetrahedron, 1998, 54, 1647.
31. d) Palacios, F.; Aparicio, D.; García, J. Tetrahedron, 1997, 53, 2931.
32. e) Palacios, F.; Ochoa de Retana, A.; Oyarzabal, J. Heterocycles, 1998, 47, 517.
33. 10. a) Palacios, F.; Aparicio, D.; de los Santos, J. M.; Rodríguez, E. Tetrahedron, 1998, 54, 599.
34. b) Palacios, F.; Aparicio, D.; García, J. Synlett, 1994, 260.
35. c) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron, 1994, 50, 12727.
36. d) López, F.; Peláez, E.; Palacios, F.; Barluenga, J.; García, S.; Tejerina, B.; García, A. J. Org. Chem., 1994, 59, 1984.
37. 11. a) Palacios, F.; Ochoa de Retana, A.; Oyarzabal, J. Tetrahedron, 1999, 55, 3091.
38. b) Barluenga, J.; López, F.; Palacios, F. J. Organomet. Chem., 1990, 382, 61.
39. c) Barluenga, J.; López, F.; Palacios, F. Tetrahedron Lett., 1987, 28, 2875.
40. 12. For an excellent review in the synthesis of aza-alkenes see: Schantl, J. G. in "Houben Weyl. Methoden der Organische Chemie". Kropf, H.; Schaumann, E. Eds; Thieme, Stuttgart, vol. E15, 1990, p 909 and references cited therein.
41. 13. a) Attanasi, O. A.; Filippone, P.; Fiorucci, C.; Foresti, E.; Mantellini, F. J. Org. Chem., 1998, 63, 9880.
42. b) South, M. S.; Jakuboski, T. L.; Westmeyer, M. D.; Dukesherer, D. R. J. Org. Chem., 1998, 63, 8921.
43. c) South, M. S.; Jakuboski, T. L.; Westmeyer, M. D.; Dukesherer, D. R. Tetrahedron Lett., 1996, 37, 1351.
44. d) South, M. S.; Jakuboski, T. L. Tetrahedron Lett., 1995, 36, 5703.
45. e) Banert, K.; Hagedorn, M. Tetrahedron Lett., 1992, 33, 7331.
46. f) Gilchrist, T. L.; Lemos, A. J. Chem. Soc. Perkin Trans. 1, 1993, 1391 and references cited therein.
47. 14. Steininger, E. Monatsh. Chem., 1966, 97, 383.