An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H- pyrazoles in ionic liquid

Monatshefte fur Chemie

Volumn 139, Issue 9, 2008, Pages 1049-1054

  Moreira, Dayse N ^a   Frizzo, Clarissa P ^a   Longhi, Kelvis ^a   Zanatta, Nilo ^a   Bonacorso, Helio G ^a   Martins, Marcos A P ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Cyanoacetohydrazide; Enones; Halomethyl compounds; Pyrazoles

Indexed keywords

EID: 50949113165     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-008-0874-8     Document Type: Article

References (70)

1. R Mulder K Wellinga JJ Van Daalen 1975 Naturwissenschaften 62 531
2. AR Katritzky CW Rees EFV Scriven 1996 Comprehensive Heterocyclic Chemistry II 3 Elsevier Science New York
3. EC Taylor H Patel H Kumar 1992 Tetrahedron 48 8089
4. JG Lombardino IG Otterness 1977 J Med Chem 20 830
5. BS Holla PM Akberali MK Shivananda 2000 Il Farmaco 55 256
6. E Bansal VK Srivatsava A Kumar 2001 Eur J Med Chem 36 81
7. FR Souza VT Souza V Ratzlaff LP Borges MR Oliveira HG Bonacorso N Zanatta MAP Martins CF Mello 2002 Eur J Pharmcol 451 141
8. F Manna R Chimenti A Fioravanti D Bolasco P Seecci C Chimenti G Ferlini 2005 Bioorg Med Chem Lett 15 4632
9. JH Ahn HM Kim SH Jung SK Kang KR Kim SD Rhee SD Yang HG Cheon SS Kim 2004 Bioorg Med Chem Lett 14 4461
10. PY Rajendera RA Lakshmana L Prasoona K Murali KP Ravi 2005 Bioorg Med Chem Lett 15 5030
11. J Strunecka P Patocka J Connett 2004 Appl Biomed 2 141
12. B Kevin NR Park PM Kitteringham 2001 Annu Rev Pharmacol Toxicol 41 443
13. SP Sachchar AK Singh 1985 J Ind Chem Soc 62 142
14. MS Karthikeyan BS Holla NS Kumari 2007 Eur J Med Chem 42 30
15. AN Kost II Grandberg 1966 Adv Heterocycl Chem 6 347
16. Bohrisch J, Patzel M, Mugge C, Liebscher J (1991) Synthesis:1153
17. X Wang J Tan K Grozinger 2000 Tetrahedron Lett 41 4713
18. AR Katrizky M Wang S Zhang MV Voronkov 2001 J Org Chem 66 6787
19. N Haddad J Baron 2002 Tetrahedron Lett 43 2171
20. VK Aggarwal J de Vicente RV Bonnert 2003 J Org Chem 68 5381
21. YR Huang JA Katzenellenbogen 2000 Org Lett 2 2833
22. KY Lee JM Kim JN Kim 2003 Tetrahedron Lett 44 6737
23. SV Druzhinin ES Balenkova VG Nenajdenko 2007 Tetrahedron 63 7753
24. TD Penning JJ Talley SR Bertenshaw JS Carter PW Collins S Docter MJ Graneto LF Lee JW Malecha JM Miyashiro RS Rogers DJ Rogier SS Yu GD Anderson EG Burton JN Cogburn SA Gregory CM Koboldt WE Perkins K Seibert AW Veenhuizen YY Zhang PC Isakson 1997 J Med Chem 40 1347
25. L-P Song S-Z Zhu 2001 J Fluorine Chem 111 201
26. SP Singh D Kumar BG Jones MD Threadgill 1999 J Fluorine Chem 94 199
27. BC Hamper 1990 J Fluorine Chem 48 123
28. X-Q Tang C-M Hu 1995 J Fluorine Chem 73 129
29. RJ Linderman KS Kirollos 1989 Tetrahedron Lett 30 2049
30. MEF Braibante GC Colla MAP Martins 1993 J Heterocycl Chem 30 1159
31. HG Bonacorso AD Wastowski N Zanatta MAP Martins JA Naue 1998 J Fluorine Chem 92 23
32. H-B Yu W-Y Huang 1997 J Fluorine Chem 84 65
33. IH Jeong SL Jeon YK Min BT Kim 2002 Tetrahedron Lett 43 7171
34. H-B Yu W-Y Huang 1998 J Fluorine Chem 87 69
35. Tang X-Q, Hu C-M (1994) Chem Commun:631
36. Guan H-P, Tang X-Q, Luo B-H, Hu C-M (1997) Synthesis:1489
37. A Padwa 1984 1,3-Dipolar Cycloaddition Chemistry I John Wiley & Sons New York
38. R Huisgen 1963 Angew Chem Int Ed 2 565
39. ME Jung ID Trifunovich 1992 Tetrahedron Lett 33 2921
40. VK Aggarwal J Vicente RV Bonnert 2003 J Org Chem 68 5381
41. Y Nakano M Hamaguchi T Nagai 1989 J Org Chem 54 5912
42. F Foti G Grassi F Risitano 1999 Tetrahedron Lett 40 2605
43. Colla A, Clar G, Martins MAP, Krimmer S, Fischer P (1991) Synthesis:483
44. Martins MAP, Sinhorin AP, Zimmermann NEK, Zanatta N, Bonacorso HG, Bastos GP (2001) Synthesis:1959
45. Bonacorso HG, Bittencourt SRT, Lourega RV, Flores AFC, Zanatta N, Martins MAP (2000) Synthesis:1431
46. MAP Martins AFC Flores GP Bastos N Zanatta HG Bonacorso 1999 J Heterocycl Chem 36 837
47. MAP Martins W Cunico CMP Pereira AP Sinhorin AFC Flores HG Bonacorso N Zanatta 2004 Curr Org Synth 1 39
48. AFC Flores N Zanatta A Rosa S Brondani MAP Martins 2002 Tetrahedron Lett 43 5005
49. Bonacorso HG, Wastowski AD, Muniz MN, Zanatta N, Martins MAP (2002) Synthesis:1079
50. VG Nenajdenko AV Sanin ES Balenkova 1997 Molecules 2 186
51. Tietze F, Meier H, Voss E (1988) Synthesis:274
52. TD Penning JJ Talley SR Bertenshaw JS Carter PW Collins S Docter MJ Graneto LF Lee JW Malecha JM Miyashiro RS Rogers DJ Rogier SS Yu GD Anderson EG Burton JN Cogburn SA Gregory CM Koboldt WE Perkins K Seibert AW Veenhuizen YY Zhang PC Isakson 1997 J Med Chem 40 1347
53. SM Sakya B Rast 2003 Tetrahedron Lett 44 7629
54. HG Bonacorso AD Wastowski N Zanatta MAP Martins 2000 Synth Commun 30 1457
55. E Zouaoui MM El Gaied 2003 J Chem Res [S] 4 242
56. MDP Salehi M Baghbanzadeh 2007 Monatsh Chem 138 1191
57. A Shaabani E Soleimani M Darvishi 2007 Monatsh Chem 138 43
58. A Shaabani A Maleki 2007 Monatsh Chem 138 51
59. A Shaabani A Rahmati F Elham AH Rezavam 2007 Monatsh Chem 138 615
60. A Shaabani A Rahmati AH Rezavam M Sharifi 2006 Monatsh Chem 137 77
61. MAP Martins EA Guarda CP Frizzo E Scapin P Beck AC Costa N Zanatta HG Bonacorso 2006 J Mol Catal A: Chem 266 100
62. C Chiappe DJ Pieraccini 2005 Phys Org Chem 18 275
63. H Olivier-Bourbigou L Magna 2002 J Mol Catal A: Chem 182-183 419
64. MJS Dewar EG Zoebisch EF Healey JJP Stewart 1985 J Am Chem Soc 107 3902 HyperChem Hypercube Inc. Waterloo Ontario Canada 2002
65. MAP Martins AFC Flores RA Freitag N Zanatta M Hörner AJ Bortoluzzi 1997 Spectrosc Lett 30 661
66. SI Vdovenko II Gerus J Wójcik 2001 J Phys Org Chem 14 533
67. R Souza PAZ Suarez CS Consorti J Dupont 2002 Org Synth 79 236
68. Sheldrick GM, SHELXS-97 (1997) Program for Crystal Structure Solution, University of Göttingen, Germany
69. Sheldrick GM, SHELXL-97 (1997) Program for Crystal Structure Refinement, University of Göttingen, Germany
70. LJ Farrugia ORTEP-III for Windows 1997 J Appl Cryst 30 565