Synthesis of ferrocenyl pyrazoles by the reaction of 3-ferrocenylpropynal with hydrazinium salts

Journal of Organometallic Chemistry

Volumn 693, Issue 1, 2008, Pages 145-154

  Zora, Metin ^a   Pinar, Ayşe Nur ^a   Odabaşoǧlu, Mustafa ^b   Büyükgüngör, Orhan ^b   Turgut, Günseli ^c  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b ONDOKUZ MAYIS UNIVERSITY   (Turkey)

^c AKDENIZ UNIVERSITY   (Turkey)

Author keywords

Condensation; Cyclization; Ferrocene; Hydrazine; Propynal; Pyrazole

Indexed keywords

CONDENSATION; CYCLIZATION; ETHANOL; HYDRAZINE; IRON COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

FERROCENE; PROPYNAL; PYRAZOLE;

AROMATIC COMPOUNDS;

EID: 36749015596     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.10.035     Document Type: Article

References (81)

1. Elguero J. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II vol. 3 (1996), Pergamon Press, Oxford 1
2. Lee K.Y., Kim J.M., and Kim J.N. Tetrahedron Lett. 44 (2003) 6737 and references cited therein
3. For selected references, see:. Lan R., Liu Q., Fan P., Lin S., Fernando S.R., McCallion D., Pertwee R., and Makriyannis A. J. Med. Chem. 42 (1999) 769
4. Komeda S., Lutz M., Spek A.L., Chikuma M., and Reedijk J. Inorg. Chem. 39 (2000) 4230
5. Djuric S.W., BaMaung N.Y., Basha A., Liu H., Luly J.R., Madar D.J., Sciotti R.J., Tu N.P., Wagenaar F.L., Wiedeman P.E., Zhou X., Ballaron S., Bauch J., Chen Y.W., Chiou X.G., Fey T., Gauvin D., Gubbins E., Hsieh G.C., Marsh K.C., Mollison K.W., Pong M., Shaughnessy T.K., Sheets M.P., Smith M., Trevillyan J.M., Warrior U., Wegner C.D., and Carter G.W. J. Med. Chem. 43 (2000) 2975
6. Selwood D.L., Brummell D.G., Budworth J., Burtin G.E., Campbell R.O., Chana S.S., Charles I.G., Fernandez P.A., Glen R.C., Goggin M.C., Hobbs A.J., Kling M.R., Liu Q., Madge D.J., Meillerais S., Powell K.L., Reynolds K., Spacey G.D., Stables J.N., Tatlock M.A., Wheeler K.A., Wishart G., and Woo C.K. J. Med. Chem. 44 (2001) 78
7. Francisco M.E.Y., Seltzman H.H., Gilliam A.F., Mitchell R.A., Rider S.L., Pertwee R.G., Stevenson L.A., and Thomas B.F. J. Med. Chem. 45 (2002) 2708
8. Haque T.S., Tadesse S., Marcinkeviciene J., Rogers M.J., Sizemore C., Kopcho L.M., Amsler K., Ecret L.D., Zhan D.L., Hobbs F., Slee A., Trainor G.L., Stern A.M., Copeland R.A., and Combs A.P. J. Med. Chem. 45 (2002) 4669
9. Nakamura T., Sato M., Kakinuma H., Miyata N., Taniguchi K., Bando K., Koda A., and Kameo K. J. Med. Chem. 46 (2003) 5416
10. Biot C., Glorian G., Maciejewski L.A., and Brocard J.S. J. Med. Chem. 40 (1997) 3715
11. Domarle O., Blampain G., Agnanet H., Nzadiyabi T., Lebibi J., Brocard J., Maciejewski L., Biot C., Georges A.J., and Millet P. Antimicrob. Agents Chemother. 42 (1998) 540
12. Biot C., Delhaes L., N'Diaye C.M., Maciejewski L.A., Camus D., Dive D., and Brocard J.S. Bioorg. Med. Chem. 7 (1999) 2843
13. Fang J., Jin Z., Li Z., and Liu W. J. Organomet. Chem. 674 (2003) 1
14. Top S., Tang J., Vessieres A., Carrez D., Provot C., and Jaouen G. Chem. Commun. (1996) 955
15. Top S., Dauer B., Vaissermann J., and Jaouen G. J. Organomet. Chem. 541 (1997) 355
16. Top S., Vessieres A., Cabestaing C., Laios I., Leclerq G., Provot C., and Jaouen G. J. Organomet. Chem. 637-639 (2001) 500
17. Top S., Vessieres A., Leclercq G., Quivy J., Tang J., Vaissermann J., Huche M., and Jaouen G. Chem. Eur. J. 9 (2003) 5223
18. Jaouen G., Top S., Vessieres A., Leclercq G., and McGlinchey M. J. Curr. Med. Chem. 11 (2004) 2505
19. For a list of ferrocenyl compounds evaluated as pharmaceuticals, see:. Allardyce C.S., Dorcier A., Scolaro C., and Dyson P. J. Appl. Organomet. Chem. 19 (2005) 1 and references cited therein
20. For the recent examples, see:. Georgopoulou A.S., Mingos D.M.P., White A.J.P., Williams D.J., Horrocks B.R., and Houlton A. J. Chem. Soc., Dalton Trans. (2000) 2969
21. Thomas J.L., Howarth J., Hanlon K., and McGuirk D. Tetrahedron Lett. 41 (2000) 413
22. Sierra M.A., Mancheno M.J., Vicente R., and Gomez-Galleo M. J. Org. Chem. 66 (2001) 8920
23. Bonini B.F., Femoni C., Comes-Franchini M., Fochi M., Mazzanti G., Ricci A., and Varchi G. Synlett (2001) 1092
24. Zora M., and Gungor E.U. Tetrahedron Lett. 42 (2001) 4733
25. Zora M., Yucel B., and Peynircioglu N.B. J. Organomet. Chem. 656 (2002) 11
26. Zora M., Yucel B., and Acikalin S. Tetrahedron Lett. 44 (2003) 2237
27. Zora M., Kokturk M., and Eralp T. Tetrahedron 62 (2006) 10344
28. Zora M., Acikgoz C., Tumay T.A., Odabasoglu M., and Buyukgungor O. Acta Crystallogr., Sect. C 62 (2006) m327
29. Zora M., Acikgoz C., Odabasoglu M., and Buyukgungor O. J. Organomet. Chem. 692 (2007) 1571
30. Kivrak A., and Zora M. J. Organomet. Chem. 692 (2007) 2346
31. Zora M., Tumay T.A., and Buyukgungor O. Tetrahedron 63 (2007) 4018
32. The literature on pyrazoles is extensive. Only a few of the most recent references are given here:. Katritzky A.R., Wang M., Zhang S., Voronkov M.V., and Steel P.J. J. Org. Chem. 66 (2001) 6787
33. Gupton J.T., Clough S.C., Miller R.B., Norwood B.K., Hickenboth C.R., Chertudi I.B., Cutro S.R., Petrich S.A., Hicks F.A., Wilkinson D.R., and Sikorski J.A. Tetrahedron 58 (2002) 5467
34. Lee K.Y., Kim J.M., and Kim J.N. Tetrahedron Lett. 44 (2003) 6737
35. Norris T., Colon-Cruz R., and Ripin D.H.B. Org. Biomol. Chem. 3 (2005) 1844
36. Curini M., Rosati O., Campagna V., Montanari F., Cravotto G., and Boccalinic M. Synlett (2005) 2927
37. Ahmed M.S.M., Kobayashi K., and Mori A. Org. Lett. 7 (2005) 4487
38. Xie F., Cheng G., and Hu Y. J. Comb. Chem. 8 (2006) 286
39. Suryakiran N., Reddy T.S., Latha K.A., Prabhakar P., Yadagiri K., and Venkateswarlu Y. J. Mol. Cat. A 258 (2006) 371
40. Dirat O., Clipson A., Elliott J.M., Garrett S., Jones A.B., Reader M., and Shaw D. Tetrahedron Lett. 47 (2006) 1729
41. Heller S.T., and Natarajan S.R. Org. Lett. 8 (2006) 2675
42. Deng X., and Mani N.S. Org. Lett. 8 (2006) 3505
43. Martin R., Rivero M.R., and Buchwald S.L. Angew. Chem., Int. Ed 45 (2006) 7079
44. Garcia H., Iborra S., and Miranda M.A. Heterocycles 32 (1991) 1745
45. Baldwin J.E., Pritchard G.J., and Rathmell R.E. J. Chem. Soc., Perkin Trans. 1 (2001) 2906
46. Chang K.T., Choi Y.H., Kim S.H., Yoon Y.J., and Lee W.S. J. Chem. Soc., Perkin Trans. 1 (2002) 207
47. Adamo M.F.A., Adlington R.M., Baldwin J.E., Pritchard G.J., and Rathmella R.E. Tetrahedron 59 (2003) 2197
48. Bishop B.C., Brands K.M.J., Gibb A.D., and Kennedy D.J. Synthesis (2004) 43
49. Dastrup D.M., Yap A.H., Weinreb S.M., Henryb J.R., and Lechleiter A.J. Tetrahedron 60 (2004) 901
50. Smith C.D., Tchabanenko K., Adlington R.M., and Baldwin J.E. Tetrahedron Lett. 47 (2006) 3209
51. Bagley M.C., Lubinu M.C., and Mason C. Synlett (2007) 704
52. Hauser C.R., and Lindsay J.K. J. Org. Chem. 22 (1957) 482
53. Niedenzu K., Serwatowski J., and Trofimenko S. Inorg. Chem. 30 (1991) 524
54. Shvekhgeimer G.A., Zvolinskii V.I., Litim M., and Terent'ev P.B. Metalloorganicheskaya Khimiya 5 (1992) 376
55. Puciova M., Ertl P., and Toma S. Collect. Czech. Chem. Commun. 59 (1994) 175
56. Almirante N., Cerri A., Fedrizzi G., Marazzi G., and Santagostino M. Tetrahedron Lett. 39 (1998) 3287
57. Burckhardt U., Drommi D., and Togni A. Inorg. Chim. Acta 296 (1999) 183
58. Abran A., Csampai A., Kotschy A., Barabas O., and Sohar P. J. Mol. Struct. 569 (2001) 185
59. Tang L.F., Jia W.L., Wang Z.H., Chai J.F., and Wang J.T. J. Organomet. Chem. 637-639 (2001) 209
60. Glas H., Pleier A.K., Herdtweck E., and Thiel W.R. J. Organomet. Chem. 684 (2003) 376
61. Lopez E.A.V., Klimova E.I., Klimova T., Toledano C.A., Ramirez L.R., Toscano R.A., and Garcia M.M. Synthesis (2004) 2471
62. Klimova E.I., Lopez E.A.V., and Klimova T. J. Heterocyclic. Chem. 42 (2005) 265
63. Joksovic M., Ratkovic Z., Vukicevic M., and Vukicevic R.D. Synlett (2006) 2581
64. Shi Y.C., Zhu B.B., and Sui C.X. Acta Crystallogr., Sect. E 62 (2006) m2389
65. Shi Y.C., Sui C.X., Cheng H.J., and Zhu B.B. J. Chem. Cryst. 37 (2007) 407
66. Shi Y.C., Zhu B.B., and Ng S.W. Acta Crystallogr., Sect. E 63 (2007) m1385
67. Mochida T., Shimizu F., Shimizu H., Okazawa K., Sato F., and Kuwahara D. J. Organomet. Chem. 692 (2007) 1834
68. Ozcubukcu S., Schmitt E., Leifert A., and Bolm C. Synthesis (2007) 389
69. Zora M., and Gormen M. J. Organomet. Chem. 692 (2007) 5026
70. M. Zora, G. Turgut, M. Gormen, in: Abstracts of Papers, 230th National Meeting of American Chemical Society, Washington, DC, USA; August 28-September 1, 2005 (ORGN 138).
71. Doisneau G., Balavoine G., and Fillebeen-Khan T. J. Organomet. Chem. 425 (1992) 113
72. Auffrant A., and Diederich F. Helv. Chim. Acta 87 (2004) 3085
73. Polin J., and Schottenberger H. In: Boeckman Jr. R.K. (Ed). Organic Syntheses vol. 73 (1996), Wiley, New York 262
74. Richards C.J. In: Gibson S.E., Harwood L.M., and Moody C.J. (Eds). Transition Metals in Organic Synthesis (1997), Oxford University Press 68
75. Turgut G., Zora M., Odabasoglu M., Ersanli C.C., and Buyukgungor O. Acta Crystallogr., Sect. C 61 (2005) o321
76. Elguero J., Marzin C., and Roberts J.D. J. Org. Chem. 39 (1974) 357
77. Aguilar-Parrilla F., Cativiela C., de Villegas D.D., Elguero J., Foces-Foces C., Laureiro J.I.G., Cano F.H., Limbach H.H., Smith J.A.S., and Toiron C. J. Chem. Soc., Perkin Trans. 2 (1992) 1737
78. de Paz J.L.G., Elguero J., Foces-Foces C., Liamas-Saiz A.L., Aguilar-Parrilla F., Klein O., and Limbach H.H. J. Chem. Soc., Perkin Trans. 2 (1997) 101
79. Garcia M.A., Lopez C., Claramunt R.M., Kenz A., Pierrot M., and Elguero J. Helv. Chim. Acta 85 (2002) 2763
80. Etter M.C. Acc. Chem. Res. 23 (1990) 120
81. 3 solvent as indicated by Solvent Correction CHN Calculator, which is available at http://www.che.hw.ac.uk/research/services/solvent.html.