Reaction of hydrazines and hydroxylamine with trifluoromethyl-β-diketones: Synthesis of trifluoromethylpyrazole and isoxazole derivatives

Heterocycles

Volumn 75, Issue 12, 2008, Pages 2893-2929

  Kumar, Vinod ^a   Aggarwal, Ranjana ^a   Singh, Shiv P ^a  

^a KURUKSHETRA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 60049091979     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-08-634     Document Type: Review

References (87)

1. R. G. Micetich and R. B. Rastogi, Canad. Pat., 1982, 1, 130, 808
2. Micetich R.G., and Rastogi R.B. Chem. Abstr. 98 (1983) 72087
3. M. Wolf, U S Pat., 1966, 3, 284, 464
4. Wolf M. Chem. Abstr. 68 (1968) 49599
5. K. Moedritzer, L. F. Lee, M. D. Rogers, D. K. Anderson, R. K. Singh, B. J. Gaede, and L.L Torrence, Eur. Pat, 1988, 295, 233
6. Moedritzer K., Lee L.F., Rogers M.D., Anderson D.K., Singh R.K., Gaede B.J., and Torrence L.L. Chem. Abstr. 111 (1989) 35509
7. K. Moedritzer and M. D. Rogers, Eur. Pat, 1990, 371, 947
8. Moedritzer K., and Rogers M.D. Chem. Abstr. 113 (1990) 211973
9. Morimoto K., Makino K., Yamamoto S., and Sakata G. J. Heterocycl. Chem. 27 (1990) 807
10. Kurumbail R.G., Stevens A.M., Gierse J.K., McDonald J.J., Stegeman R.A., Pak J.Y., Gildehaus D., Miyashiro J.M., Penning T.D., Seibert K., Isakson P.C., and Stallings W.C. Nature 384 (1996) 644
11. Desiraju G.R., Gopalakrishnan B., Jetti K.K.R., Raveendra D., Sarma J.A.R.P., and Subramanya H.S. Molecules 5 (2000) 945
12. Kees K.L., Fitzgerald J.J., Steiner K.E., Mattes J.F., Mihan B., Tosi T., Mondoro D., and McCaleb M.L. J. Med. Chem. 39 (1996) 3920
13. Kudo N., Furuta S., Taniguchi M., Endo T., and Sato K. Chem. Pharm. Bull. 47 (1999) 857
14. Jung J.C., Watkins E.B., and Avery M.A. Tetrahedron 58 (2002) 3639
15. Peat A.J., Townsend C., Mckay M.C., Garrido D., Terry C.M., Wilson J.L.R., and Thomson S.A. Bioorg. Med. Chem. Lett. 14 (2004) 813
16. Pinto D.J.P., Orwat M.J., Wang S., Fevig J.M., Quan M.L., Amparo E., Cacciola J., Rossi K.A., Alexander R.S., Smallwood A.M., Luettgen J.M., Liang L., Aungst B.J., Wright M.R., Knabb R.M., Wong P.C., Wexler R.R., and Lam P.Y.S. J. Med. Chem. 44 (2001) 566
17. Wong P.C., Pinto D.J.P., and Knabb R.M. Cardiovascular Drug Reviews 20 (2002) 137
18. Habeeb A.G., Rao P.N.P., and Knaus E.E. J. Med. Chem. 44 (2001) 3039
19. Singh S.K., Reddy M.S., Shivaramakrishna S., Kavitha D., Vasudev R., Babu J.M., Sivalakshmidevi A., and Rao Y.K. Tetrahedron Lett. 45 (2004) 7679
20. Singh S.K., Reddy P.G., Rao K.S., Lohray B.B., Misra P., Rajjak S.A., Rao Y.K., and Venkateswarula A. Bioorg. Med. Chem. Lett. 14 (2004) 499
21. Carr J.B., Durham H.G., and Hass D.K. J. Med. Chem. 20 (1977) 934
22. Garg U., Sareen V., Khatri V., and Chugh S. Indian J. Heterocycl. Chem. 12 (2002) 139
23. Gupta U., Sareen V., Khatri V., and Chugh S. Indian J. Heterocycl. Chem. 14 (2005) 265
24. Sharma K., Sareen V., and Khatri V. Indian J. Heterocycl. Chem. 15 (2005) 47
25. Koľtsov A.I., and Kheifets G.M. Usp Khim. 40 (1971) 1646
26. Koľtsov A.I., and Kheifets G.M. Chem. Abstr. 76 (1972) 45282d
27. Moriyasu M., Kato A., and Hashimoto Y. J. Chem. Soc., Perkin Trans. 2 (1986) 515
28. H. A. Wagner, U S. Pat., 1965, 3, 200, 128.
29. Wagner H.A. Chem. Abstr. 63 (1965) 13272b
30. Nishiwaki T. J. Chem. Soc. (B) (1967) 885
31. Trofimenko S. J. Am. Chem. Soc. 89 (1967) 3165
32. Portnoy S. J. Heterocycl. Chem. 6 (1969) 223
33. Secor H.V., and DeBardeleben J.F. J. Med. Chem. 14 (1971) 997
34. Lyga J.W., and Patera R.M. J. Heterocycl. Chem. 27 (1990) 919
35. 19F NMR Sensors for the Measurement of pH in Biological Systems", Ph.D. Thesis (1995), University of Bath
36. Elguero J., and Yranzo G.I. J. Chem. Res. (S) (1990) 120
37. Elguero J., Yranzo G.I., Laynez J., Jimenez P., Menendez M., Catalan J., De Paz J.L.G., Anvia F., and Taft R.W. J. Org. Chem. 56 (1991) 3942
38. Singh S.P., Sehgal S., Tarar L.S., and Dhawan S.N. Indian. J. Chem. 29B (1990) 310
39. Zimmer H., and Amer A. Heterocycles 26 (1987) 1177
40. Amer A., Rashed N., Rahman M.M.A., and Zimmer H. Heterocycles 26 (1987) 1277
41. Joshi K.C., Jain R., Dandia A., and Sharma K. J. Heterocycl. Chem. 25 (1988) 1641
42. Claire P.P.K., Coe P.I., Jones C.J., and MeCleverty J.A. J. Fluorine Chem. 51 (1991) 283
43. Threadgill M.D., Heer A.K., and Jones B.G. J. Fluorine Chem. 65 (1993) 21
44. Singh S.P., Kumar D., Savita M.D., and Threadgill. Indian J. Chem. 31B (1992) 233
45. Singh S.P., Kumar D., and Kapoor J.K. J. Chem. Res. (S) (1993) 163
46. Singh S.P., Kumar D., and Kapoor J.K. J. Chem. Res. (M) (1993) 1168
47. Singh S.P., Kapoor J.K., Kumar D., and Threadgill M.D. J. Fluorine Chem. 83 (1997) 73
48. Begtrup M., Elguero J., Faure R., Camps P., Estopa C., Ilavsky D., Fruchier A., Marzin C., and de Mendoza J. Org. Magn. Reson. 26 (1988) 134 and references cited therein
49. Begtrup M., Boyer G., Cabildo P., Cativiela C., Claramunt R.M., Elguero J., Garcia J.I., Toiron C., and Vedso P. Org. Magn. Reson. 31 (1993) 107 and references cited therein
50. Singh S.P., Vaid R.K., Prakash I., and Prakash O. Indian J. Chem. 25B (1986) 945
51. Sawhney S.N., Tomer R.K., Prakash I., and Singh S.P. Indian J. Chem. 19B (1980) 395
52. Cabildo P., Claramunt R.M., and Elguero J. Org. Magn. Reson. 22 (1984) 603
53. Bruix M., de Mendoza J., and Elguero J. Tetrahedron 43 (1987) 4663
54. Steel P.J., and Constable E.C. J. Chem. Soc. Dalton Trans. (1990) 1389
55. Singh S.P., Kumar D., Jones B.G., and Threadgill M.D. J. Fluorine Chem. 94 (1999) 199
56. Singh S.P., and Kumar D. J. Chem. Res.(S) (1997) 142
57. Singh S.P., Kumar D., Batra H., Naithani R., Rozas I., and Elguero J. Can. J. Chem. 78 (2000) 1109
58. Tanaka K., Kishida M., Maeno S., and Mitsuhashi K. Chem. Lett. (1982) 543
59. Tanaka K., Maeno S., and Mitsuhashi K. J. Heterocycl. Chem. (1985) 565
60. Linderman R.J., and Kirollos K.S.. Tetrahedron Lett. 30 (1989) 2049
61. Selivanov S.I., Goldova K.G., Abbasov Y.A., and Ershov B.A. Zh. Org. Khim. 22 (1986) 2073
62. Zefirov N.S., Kozhushkov S.I., Kuznetsova T.S., Ershov B.A., and Selivanov S.I. Tetrahedron 42 (1986) 709
63. Kartitzky A.R., Ostercamp D.L., and Yousaf T.I. Tetrahedron 43 (1987) 5171
64. Zelenin K.N., and Yakimovitch S.I. Targets Heterocycl. Syst. 2 (1998) 207
65. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogbum J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., and Isakson P.C. J. Med. Chem. 40 (1997) 1347
66. Song L., and Zhu S. J. Fluorine Chem. 111 (2001) 201
67. Denisova A.B., Sosnovskikh V.Y., Dehaen W., Toppet S., Meervelt L.V., and Bakulev V.A. J. Fluorine Chem. 115 (2002) 183
68. Sloop J.C., Bumgardner C.L., and Loehle W.D. J. Fluorine Chem. 118 (2002) 135
69. Wong P.C., Pito D.J.P., and Knabb R.M. Cardiovascular Drug Rev. 20 (2002) 137
70. Uddin M.J., Rao P.N.P., and Knaus E.E. Bioorg. Med. Chem. 11 (2003) 5273
71. Pal M., Madan M., Padakanti S., Pattabiraman V.R., Kalleda S., Vanguri A., Mullangi R., Mamidi N.V.S.R., Casturi S.R., Malde A., Gopalakrishnan B., and Yeleswarapu K.R. J. Med. Chem. 46 (2003) 3975
72. Braibante M.E.F., Clar G., and Martins M.A.P. J. Heterocycl. Chem. 30 (1993) 1159
73. Bonacorso H.G., Wastowski A.D., Zanatta N., Martins M.A.P., and Naue J.A. J. Fluorine Chem. 92 (1998) 23
74. Bonacorso H.G., Oliveira M.R., Costa M.B., Silva L.B., Zanatta N., Martins M.A.P., and Flores A.F.C. J. Braz. Chem. Soc 16 (2005) 868
75. Singh S.P., Kumar V., Aggarwal R., and Elguero J. J. Heterocycl. Chem. 43 (2006) 1003
76. Montoya V., Pons J., Antón J.G., Solans X., Bardia M.F., and Ros J. J. Fluorine Chem. 128 (2007) 1007
77. Carr J.B., Durham H.G., and Hass D.K. J. Med. Chem. 20 (1977) 934
78. Martins M.A.P., Flores A.F.C., Freitag R., and Zanatta N. J. Heterocycl. Chem. 32 (1995) 731
79. Martins M.A.P., Flores A.F.C., Freitag R.A., and Zanatta N. J. Heterocycl. Chem. 33 (1996) 1223
80. Felix C.P., Khatimi N., and Laurent A.J. J. Org. Chem. 60 (1995) 3907
81. Martins M.A.P., Siqueira G.M., Bastos G.P., Bonacorso H.G., and Zanatta N. J. Heterocycl. Chem. 33 (1996) 1619
82. Sosnovskikh V.Y., Sizon A.Y., and Usachev B.I. Russian Chem. Bull. Int. Edition 51 (2002) 1270
83. Sanz D., Claramunt R.M., Singh S.P., Kumar V., Aggarwal R., Elguero J., and Alkorta I. Mag. Res. Chem. 43 (2005) 1040
84. Kumar V., Aggarwal R., and Singh S.P. J. Fluorine Chem. 127 (2006) 880
85. Martins M.A.P., Siqueira G.M., Bastos G.P., Bonacorso H.G., and Zanatta N. J. Heterocycl. Chem. 33 (1996) 1619
86. Sosnovskikh V.Y., Sizon A.Y., and Usachev B.I. Russian Chem. Bull. Int. Edition 51 7 (2002) 1270
87. Tanaka K., Masuda H., and Mitsuhashi K. Bull. Chem. Soc. Jpn. 57 (1984) 2184