Uncatalyzed three-component synthesis of α-hydrazido phosphonates

European Journal of Organic Chemistry

Volumn , Issue 8, 2010, Pages 1450-1454

  Herrera, Raquel P ^a,b   Roca López, David ^a   Navarro Moros, Gloria ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b FUNDACIÓN ARAID   (Spain)

Author keywords

Hydrazones; Multicomponent reactions; Nucleophilic addition; Phosphonates

Indexed keywords

EID: 77649213160     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901337     Document Type: Article

References (55)

1. A. N. Pudovik, I. V Konovalova, Synthesis 1979, 81-96.
2. For a recent review on this topic, see: P. Merino, E. Marqués-López, R. P. Herrera, Adv. Synth. Catal. 2008, 350, 1195-1208, and references cited therein.
3. For selected examples, see: a) F. R. Atherton, M. J. Hall, C. H. Hassall, S. W. Holmes, R. W. Lambert, J. Lloyd, P. S. Ringrose, Antimicrob. Agents Chemother. 1980, 18, 897-905;
4. b) T. Kametani, K. Kigasawa, M. Hiiragi, K. Wakisaka, S. Haga, H. Sugi, H. Tanigawa, Y. Suzuki, K. Fukawa, O. Irino, O. Saita, S. Yamabe, Heterocycles 1981, 16, 1205-1242;
5. c) F. R. Atherton, C. H. Hassall, R. W. Lambert, J. Med. Chem. 1986, 29, 29-40.
6. a) I. A. Natchev, Liebigs Ann. Chem. 1988, 861-867;
7. b) M. K. Mao, J. E. Franz, Synthesis 1991, 920-922.
8. J. Emsley, D. Hall, The Chemistry of Phosphorus, Harper and Row, London, 1976, p. 494.
9. L. Maier, H. Spörri, Phosphorus Sulfur Silicon Relat. Elem. 1991, 61, 69-75.
10. J. Huang, R. Chen, Heteroat. Chem. 2000, 11, 480-492.
11. For selected examples, see: a) J. Bird, R. C. De Mello, G. P. Harper, D. J. Hunter, E. H. Karran, R. E. Markwell, A. J. Miles-Williams, S. S. Rahman, R. W. Ward, J. Med. Chem. 1994, 37, 158-169;
12. b) J. L. Goulet, J. F. Kinneary, P. L. Durette, R. L. Stein, R. K. Harrison, M. Izquierdo-Martin, D. W. Kuo, T.-Y. Lin, W. K. Hagmann, Bioorg. Med. Chem. Lett. 1994, 4, 1221-1224.
13. For a review, see: c) P. Kafarski, B. Lejczak, Phosphorus Sulfur Silicon Relat. Elem. 1991, 63, 193-215.
14. a) A. Paymen, K.-H. Budt, J. Spanig, B. Stowasser, D. Ruppert, Tetrahedron Lett. 1992, 33, 4549-4552;
15. b) B. Stowasser, K.-H. Budt, L. Jian-Qi, A. Paymen, D. Ruppert, Tetrahedron Lett. 1992, 33, 6625-6628;
16. c) A. Peymen, W. Stahl, K. Wagner, D. Ruppert, K.-H. Budt, Bioorg. Med. Chem. Lett. 1994, 4, 2601-2604.
17. For a review, see: V. P. Kukhar, V. A. Solodenko, Russ. Chem. Rev. 1987, 56, 856-874.
18. For a recent review, see: M. Ordóñez, H. Rojas-Cabrera, C. Cativiela, Tetrahedron 2009, 65, 17-49.
19. For some examples of hydrophosphonylation of imines catalyzed by Lewis acids, see: a) S. Lashat, H. Kunz, Synthesis 1992, 90-95;
20. b) B. C. Ranu, A. Hajra, J. Jana, Org. Lett. 1999, 1, 1141-1143;
21. c) K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670;
22. d) B. Kaboudin, R. Nazari, Tetrahedron Lett. 2001, 42, 8211-8215;
23. e) F. Xu, Y. Luo, M. Deng, Q. Shen, Eur. J. Org. Chem. 2003, 4728-4730;
24. f) S. Kudrimoti, V. R. Bommena, Tetrahedron Lett. 2005, 46, 1209-1210.
25. For reviews about N-acylhydrazones as versatile electrophiles, see: a) M. Sugiura, S. Kobayashi, Angew. Chem. Int. Ed. 2005, 44, 5176-5186;
26. b) G. K. Friestad, Eur. J. Org. Chem. 2005, 3157-3172;
27. c) S. Kobayashi, M. Sugiura, C. Ogawa, Adv. Synth. Catal. 2004, 346, 1023-1034.
28. For the only reported example, see: N. Rabasso, A. Fadel, Synthesis 2008, 2353-2362.
29. a) C. Yuan, S. Chen, R. Xie, H. Feng, L. Maier, Phosphorus Sulfur Silicon Relat. Elem. 1995, 106, 115-123;
30. b) C. Li, C. Yuan, Synthesis 1996, 507-510;
31. c) M. Kaname, K. Yoshinaga, Y. Arakawa, S. Yoshifuji, Tetrahedron Lett. 1999, 40, 7993-7994.
32. S. Inokawa, Y. Nakatsukasa, M. Horisaki, M. Yamashita, H. Yoshida, T. Ogata, Synthesis 1977, 179-180.
33. a) M. Yamashita, J. Takeuchi, K. Nakatani, T. Oshikawa, Bull. Chem. Soc. Jpn. 1985, 58, 377-378;
34. b) H. Yamamoto, T. Hanaya, H. Kawamoto, S. Inokawa, Chem. Lett. 1989, 121-124.
35. a) A. Heydari, A. Javidan, M. Schaffie, Tetrahedron Lett. 2001, 42, 8071-8073;
36. b) A. Heydari, M. Mehrdad, M. Schaffie, M. S. Abdolrezaie, R. Hajinassirei, Chem. Lett. 2002, 1146-1147;
37. c) A. Heydari, A. Arefi, Catal. Commun. 2007, 8, 1023-1026.
38. P. Diel, L. Maier, Eur. Pat. Appl. EP 1985, 143078
39. ; [Chem. Abstr. 1985, 103, 215544m].
40. For a plausible mechanism of activation of N,N-dialkylhydrazones, see: E. Marqués-López, R. P. Herrera, R. Fernández, J. M. Lassaletta, Eur. J. Org. Chem. 2008, 3457-3460.
41. For reviews about aldehyde N,N-dialkylhydrazones as neutral acyl anion equivalents, see: a) R. Fernández, J. M. Lassaletta, Synlett 2000, 1228-1240;
42. b) R. Brehme, D. Enders, R. Fernández, J. M. Lassaletta, Eur. J. Org. Chem. 2007, 5629-5660, and references therein.
43. For a review, see: D. F. Wiemer, Tetrahedron 1997, 53, 16609-16644.
44. B. Springs, P. Haake, J. Org. Chem. 1977, 42, 472-474.
45. a, values of different phosphorus nucleophiles, see: J.-N. Li, L. Liu, Y Fu, Q.-X. Guo, Tetrahedron 2006, 62, 4453-4462.
46. For reviews, see: a) L. F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
47. b) D. J. Ramón, M. Yus, Angew. Chem. Int. Ed. 2005, 44, 1602-1634;
48. c) G. Guillena, G. D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2007, 18, 693-700.
49. Unfortunately, the use of benzaldehyde or cinnamaldehyde did not afford the final products after three days of reaction and under the same reactions conditions.
50. 2, see: K. Gopalaiah, H. B. Kagan, New J. Chem. 2008, 32, 607-637.
51. 3N (20 mol%) was used as catalyst; 13 (71 %) and 14 (63%).
52. CCDC-753258 (8b) and -753259 (8c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif. The graphic views showed in Figures S1 and S2 (Supporting Information) were made with ORTEP3 software (Copyright by Farrugia, L. J. University of Glasgow, 1997-2000).
53. a) D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, W. L. Rogers, S. A. Smith, J. M. DeForrest, R. S. Oehl, E. W. Petrillo Jr., J. Med. Chem. 1995, 38, 4557-4569;
54. b) V. P. Kukhar, H. R. Hudso (Eds.), Aminophosponic and Aminophosphinic Acids: Chemistry and Biological Activity, Wiley, Chichester, 2000;
55. c) J. Huang, R. Chen, Heteroat. Chem. 2000, 11, 480-492.