One-pot parallel solution-phase synthesis of 1-substituted 4-(2-aminoethy)-1H-pyrazol-5-ols

Journal of Combinatorial Chemistry

Volumn 10, Issue 5, 2008, Pages 664-670

  Kralj, David ^a   Novak, Ana ^a   Dahmann, Georg ^b   Grošelj, Uroš ^a   Meden, Anton ^a   Svete, Jurij ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDINONE; 2 PYRROLIDONE DERIVATIVE; 2-PYRROLIDONE; ACETIC ACID; ACETIC ACID DERIVATIVE; ACETIC ACID ETHYL ESTER; AMINE; BROMINATED HYDROCARBON; HYDRAZINE DERIVATIVE; HYDROBROMIC ACID; HYDROCHLORIC ACID; LACTAM; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; MICROWAVE RADIATION; SOLUTION AND SOLUBILITY; SYNTHESIS; TEMPERATURE;

ACETATES; ACETIC ACID; AMINES; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDRAZINES; HYDROBROMIC ACID; HYDROCARBONS, BROMINATED; HYDROCHLORIC ACID; LACTAMS; MICROWAVES; MODELS, CHEMICAL; PYRAZOLES; PYRROLIDINONES; SOLUTIONS; TEMPERATURE;

EID: 53049102917     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc8000794     Document Type: Article

References (57)

1. Dolle, R. E. Solid-phase Synthesis of Heterocyclic Systems (Heterocycles Containing One Heteroatom). In Handbook of Combinatorial Chemistry. Drugs, Catalysts, Materials; Nicolaou,K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2002; Vol. 2, pp 643-684.
2. Pernerstorfer, J. Molecular Design and Combinatorial Compound Libraries. In Handbook of Combinatorial Chemistry. Drugs, Catalysts, Materials; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2002; Vol. 2, pp 725-742.
3. Dörwald, F. Z. Organic Synthesis on Solid Phase, 2nd ed.; Wiley-VCH Verlag GmbH:Weinheim, Germany, 2002; pp 1-504.
4. (a) Dolle, R. E.; Nelson, K. H., Jr. J. Comb. Chem. 1999, 1, 235-282.
5. (b) Dolle, R. E. J. Comb. Chem. 2000, 2, 383-433.
6. (c) Dolle, R. E. J. Comb. Chem. 2001, 3, 1-41.
7. (d) Dolle, R. E. J. Comb. Chem. 2002, 4, 369-418.
8. (e) Dolle, R. E. J. Comb. Chem. 2003, 5, 693-753.
9. (f) Dolle, R. E. J. Comb. Chem. 2004, 6, 623-679.
10. (g) Dolle, R. E. J. Comb. Chem. 2005, 7, 739-798.
11. (h) Dolle, R. E.; Le Bourdonnec, B.; Morales, G. A.; Moriarty, K. J.; Salvino, J. M. J. Comb. Chem. 2006, 8, 597-635.
12. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854, and references therein.
13. (a) Patrick, G. L. An Introduction to Medicinal Chemistry, 3rd ed.; Oxford University Press: Oxford, 2005; pp 3-741.
14. (b) Kazuta, Y.; Hirano, K.; Natsume, K.; Yamada, S.; Kimura, R.; Matsumoto, S.-i.; Furuichi, K.; Matsuda, A.; Shuto, S. J. Med. Chem. 2003, 46, 1980-1989.
15. (c) Liebscher, J.; Patzel, M. Synlett 1994, 471-478.
16. (d) Elsner, J.; Boeckler, F.; Davidson, K.; Sugden, D.; Gmeiner, P. Bioorg. Med. Chem. 2006, 14, 1949-1958.
17. (e) Nenajdenko, V. G.; Zakurdaev, E. P.; Gololobov, A. M.; Balenkova, E. S. Russ. Chem. Bull. 2005, 54, 220-225.
18. (f) Marshall, D. R.; Rodriguez, G.; Thomson, D. S.; Nelson, R.; Capolina, A. Bioorg. Med. Chem. Lett. 2007, 17, 315-319.
19. For a review see: (a) Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433-2480.
20. (b) Stanovnik, B.; Svete, J. Synlett 2000, 1077-1091.
21. (c) Stanovnik, B.; Svete, J. Targets Heterocycl. Syst. 2000, 4, 105-137.
22. For a review see: (a) Svete, J. ARKIVOC 2006, vii, 35-46.
23. (b) Stanovnik, B.; Svete, J. Mini-Rev. Org. Chem. 2005, 2, 211-224.
24. (c) Svete, J. Monatsh. Chem. 2004, 135, 629-641.
25. (d) Svete, J. J. Heterocycl. Chem. 2002, 39, 437-454.
26. Some recent publications: (a) Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron: Asymmetry 2008, 19, 330-342.
27. (b) Wagger, J.; Grošelj, U.; Meden, A.; Svete, J.; Stanovnik, B. Tetrahedron 2008, 64, 2801-2815.
28. (c) Rečnik, S.; Meden, A.; Stanovnik, B.; Svete, J. Aust. J. Chem. 2008, 61, 107-114.
29. (d) Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron: Asymmetry 2007, 18, 2746-2757.
30. (e) Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron: Asymmetry 2007, 18, 2365-2376.
31. (f) Wagger, J.; Golič Grdadolnik, S.; Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron: Asymmetry 2007, 18, 464-475.
32. Pire, S.; Bevk, D.; Golič Grdadolnik, S.; Svete, J. ARKIVOC 2003, xiv, 37-48.
33. Westman, J.; Lundin, R. Synthesis 2003, 1025-1030.
34. Čebašek, P.; Wagger, J.; Bevk, D.; Jakše, R.; Svete, J.; Stanovnik, B. J. Comb. Chem. 2004, 6, 356-362.
35. Čebašek, P.; Bevk, D.; Pirc, S.; Stanovnik, B.; Svete, J. J. Comb. Chem. 2006, 8, 95-102.
36. Malavašič Č.; Brulc, B.; Čebašek, P.; Dahmann, G.; Heine, N.; Bevk, D.; Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. J. Comb. Chem. 2007, 9, 219-229.
37. For a review see: (a) Elguero, J. Pyrazoles. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.;Elsevier Science Ltd.: Oxford, 1996; Vol. 3; pp 1-75.
38. (b) Stanovnik, B.; Svete, J. Pyrazoles. In Science of Synthesis, Houben-Weyl Methods of Organic Transformations; Neier, R., Ed.; Georg Thieme Verlag: Stuttgart, 2002; Vol. 12, pp 15-225.
39. (a) Hanzlowsky, A.; Jelenčič, B.; Rečnik, S.; Svete, J.; Golobič, A.; Stanovnik, B. J. Heterocycl. Chem. 2003, 40, 487.
40. (b) Kralj, D.; Mecinovič, J.; Bevk, D.; Grošelj, U.; Stanovnik, B.; Svete, J. Heterocycles 2006, 68, 897-914.
41. Grošelj, U.; Bevk, D.; Jakše, R.; Rečnik, S.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron 2005, 61, 3991-3998.
42. (a) Škof, M.; Svete, J.; Stanovnik, B. Heterocycles 2000, 53, 339-346.
43. (b) Uršič, U.; Bevk, D.; Pirc, S.; Pezdirc, L.; Stanovnik, B.; Svete, J. Synthesis 2006, 2376-2384.
44. Pirc, S.; Bevk, D.; Golobič, A.; Stanovnik, B.; Svete, J. Helv. Chim. Acta 2006, 89, 30-44.
45. Mihelič, D.; Jakše, R.; Svete, J.; Stanovnik, B.; Golio Grdadolnik, S. J. Heterocycl. Chem. 2001, 38, 1307-1312.
46. Kralj, D.; Grošelj, U.; Meden, A.; Dahmann, G.; Stanovnik, B.; Svete, J. Tetrahedron 2007, 63, 11213-11222.
47. Giovannini, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1989, 54, 228-234.
48. Yasuda, N.; Hsiao, Y.; Jensen, M. S.; Rivera, N. R.; Yang, C.; Wells, K. M.; Yau, J.; Palucki, M.; Tan, L.; Dormer, P. G.; Volante, R. P.; Huges, D. L.; Reider, P. J. J. Org. Chem. 2004, 69, 1959-1966.
49. (a) Bowler, A. N.; Dinsmore, A.; Doyle, P. M.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1997, 1297-1306.
50. (b) Dinsmore, A.; Doyle, P. M.; Young, D. W. Tetrahedron Lett. 1995, 36, 7503-7506.
51. (c) Bowler, A. N.; Doyle, P. M.; Young, D. W. J. Chem. Soc., Chem. Commun. 1991, 314-316.
52. Druey, J.; Meier, K.; Eichenberger, K. Helv. Chim. Acta 1954, 37, 121-133.
53. Libermann, D.; Rouaix, A. Bull. Soc. Chim. Fr. 1959, 1793-1798.
54. Stanovnik, B.; Tišler, M. Tetrahedron 1967, 23, 387-395.
55. Pollak, A.; Trešler, M. Tetrahedron 1966, 22, 2073-2079.
56. Kovačič, A.; Stanovnik, B.; Tišler, M. J. Heterocycl. Chem. 1968, 5, 351-354.
57. In the case of the free hydrazine derivative 4 (1 mmol), 1 equiv of 37% hydrochloric acid (0.1 mL, 1 mmol) was also added.