Fluorinated alcohols: A magic medium for the synthesis of heterocyclic compounds

Journal of Fluorine Chemistry

Volumn 172, Issue , 2015, Pages 51-61

  Khaksar, Samad ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Fluorinated solvent; Heterocyclic; Hydrogen bonding; Multicomponent; Recyclable

Indexed keywords

EID: 84922709216     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2015.01.008     Document Type: Review

References (133)

1. I.A. Shuklov, N.V. Dubrovina, and A. Børner Synthesis 2007 2925 2943 (For reviews on fluorous alcohols, see)
2. J.-P. Bégué, D. Bonnet-Delpon, and B. Crousse Synlett 2004 18 29
3. J.-P. Bégué, D. Bonnet-Delpon, and B. Crousse J.A. Gladysz, D.P. Curran, I.T. Horvath, Handbook of Fluorous Chemistry 2004 Wiley-VCH Weinheim 341 350
4. M. Willot, J.C. Chen, and J. Zhu Synlett 2009 577 580
5. M.O. Ratnikov, V.V. Tumanov, and W.A. Smit Angew. Chem., Int. Ed. 47 2008 9739 9742
6. K. De, J. Legros, B. Crousse, and D. Bonnet-Delpon Tetrahedron 64 2008 10497 10500
7. M. Westermaier, and H. Mayr Chem. Eur. J. 14 2008 1638 1647
8. A. Heydari, S. Khaksar, and M. Tajbakhsh Synthesis 2008 3126 3130
9. T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga, and Y. Kita Chem. Commun. 2007 1224 1226
10. K. Hata, H. Hamamoto, Y. Shiozaki, S.B. Cämmerer, and Y. Kita Tetrahedron 63 2007 4052 4060
11. N.V. Dubrovina, I.A. Shuklov, M.N. Birkholz, D. Michalik, R. Paciello, and A. Börner Adv. Synth. Catal. 349 2007 2183 2187
12. H. Yagi, and D.M. Jerina J. Org. Chem. 72 2007 9983 9990
13. A. Jean, J. Cantat, D. Bérard, D. Bouchu, and S. Canesi Org. Lett. 9 2007 2553 2556
14. J. Legros, B. Crousse, M. Ourévitch, and D. Bonnet-Delpon Synlett 2006 1899 1902
15. A. Di Salvo, M. David, B. Crousse, and D. Bonnet-Delpon Adv. Synth. Catal. 348 2006 118 124
16. J.F. Povey, C.M. Smales, S.J. Hassard, and M.J. Howard J. Struct. Biol. 157 2007 329 338
17. M. Hudlicky Chemistry of Organic Fluorine Compounds second ed. 1992 Ellis-Horwood New York, NY
18. R.E. Banks, B.E. Smart, and J.C. Tatlow Organic Fluorine Chemistry. Principles and Applications 1994 Plenum New York, NY
19. K. Uneyama Organofluorine Chemistry 2006 Blackwell Publishing Oxford (Chapter 4)
20. J.A. Gladysz, D.P. Curran, and I.T. Horvath Handbook of Fluorous Chemistry 2004 Wiley-VCH Verlag GmbH & Co.: KGaA Weinheim, Germany
21. K.F. Purcell, J.A. Stikeleather, and S.D. Brunk J. Am. Chem. Soc. 91 1969 4019 4027
22. M.J. Kamlet, J.-L. Abboud, M.H. Abrham, and R.W. Taft J. Org. Chem. 48 1983 2877 2887
23. W.J. Middleton, and R.V. Lindsey Jr. J. Am. Chem. Soc. 86 1964 4948 4952
24. L. Eberson, M.P. Hartshorn, O. Persson, and F. Radner Chem. Commun. 1996 2105 2112 (and references therein)
25. K.S. Ravikumar, J.P. Bégué, and D. Bonnet-Delpon Tetrahedron Lett. 39 1998 3141 3144
26. K.S. Ravikumar, Y.M. Zhang, J.P. Bégué, and D. Bonnet-Delpon Eur. J. Org. Chem. 1998 2937 2940
27. K. Žmitek, S. Stavber, M. Zupan, D. Bonnet-Delpon, S. Charneau, P. Grellier, and J. Iskra Bioorg. Med. Chem. 14 2006 7790 7795
28. G.J. ten Brink, B.C.M. Fernandes, M.C.A. van Vliet, I.W.C.E. Arends, and R.A. Sheldon J. Chem. Soc., Perkin Trans. 1 2001 224 228
29. A. Berkessel, M.R.M. Andreae, H. Schmickler, and J. Lex Angew. Chem. Int. Ed. 4 2002 4481 4484
30. A. Berkessel, and M.R.M. Andreae Tetrahedron Lett. 42 2001 2293 2295
31. J. Iskra, D. Bonnet-Delpon, and J.P. Bégué Tetrahedron Lett. 43 2002 1001 1003
32. G.-J. ten Brink, J.-M. Vis, I.W.C.E. Arends, and R.A. Sheldon J. Org. Chem. 66 2001 2429 2433
33. M. Matsumoto, and H. Kobayashi Heterocycles 24 1986 2443 2447
34. S. Kobayashi, H. Tanaka, H. Amii, and K. Uneyama Tetrahedron 59 2003 1547 1552
35. A. Berkessel, and J.A. Adrio J. Am. Chem. Soc. 128 2006 13412 13420
36. K. Neimann, and R. Neumann Org. Lett. 2 2000 2861 2863
37. M.C.A. van Vliet, I.W.C.E. Arends, and R.A. Sheldon Synlett 2001 248 250
38. S.P. de Visser, J. Kaneti, R. Neumann, and S. Shaik J. Org. Chem. 68 2003 2903 2912
39. J. Legros, B. Crousse, D. Bonnet-Delpon, and J.P. Bégué Eur. J. Org. Chem. 2002 3290 3293
40. M.C.A. van Vliet, I.W.C.E. Arends, and R.A. Sheldon J. Chem. Soc., Perkin Trans. 1 2000 377 380
41. S. Khaksar, and S.M. Talesh J. Fluorine Chem. 140 2012 95 98
42. K. De, J. Legros, B. Crousse, and D. Bonnet-Delpon J. Org. Chem. 74 2009 6260 6265
43. A. Heydari, S. Khaksar, and M. Tajbakhsh Synthesis 2008 3126 3130
44. J. Choy, S. Jaime-Figueroa, and T. Lara-Jaime Tetrahedron Lett. 51 2010 2244 2246
45. K. Azzouzi-Zriba, D. Bonnet-Delpon, and B. Crousse J. Fluorine Chem. 132 2011 811 814
46. S. Khaksar, A. Heydari, M. Tajbakhsh, and H.R. Bijanzadeh J. Fluorine Chem. 131 2010 106 110
47. V. Kesavan, D. Bonnet-Delpon, and J.P. Bégué Tetrahedron Lett. 41 2000 2895 2898
48. A.R. Katritzky, C.W. Ress, and E.F.V. Scriven Comprehensive Heterocyclic Chemistry II vols. 1-9 1996 Pergamon Oxford, UK
49. A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, and R.J.K. Taylor Comprehensive Heterocyclic Chemistry III vols. 1-13 2008 Pergamon Oxford, UK
50. G. Kirsch, S. Hesse, and A. Comel Curr. Org. Synth. 1 2004 47 63
51. S.V. Druzhinin, E.S. Balenkova, and V.G. Nenajdenko Tetrahedron 63 2007 7753 7808
52. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, and H.G. Bonacorso Chem. Rev. 108 2008 2015 2050
53. A.T. Balaban, D.C. Oniciu, and A.R. Katritzky Chem. Rev. 104 2004 2777 2812
54. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol, and P. Machado Chem. Rev. 109 2009 4140 4182
55. J.G. Lombardino, and E.H. Wiseman J. Med. Chem. 17 1974 1182 1188
56. F. Gallagher, S.M. Fier-Thompson, R.S. Garigipati, M.E. Sorenson, J.M. Smietana, D. Lee, P.E. Bender, J.C. Lee, J.T. Laydon, D.E. Griswold, M.C. Chabot-Fletcher, J.J. Breton, and J.L. Adams Bioorg. Med. Chem. Lett. 5 1995 1171 1176
57. M. Misono Chem. Commun. 2001 1141 1152
58. U. Ucucu, N.G. Karaburun, and I. Isikdag Farmaco 56 2001 285 290
59. L.L. Chang, K.L. Sidler, M.A. Cascieri, S. de Laszlo, G. Koch, B. Li, M. MacCoss, N. Mantlo, S. O'Keefe, M. Pang, A. Rolando, and W.K. Hagmann Bioorg. Med. Chem. Lett. 11 2001 2549 2553
60. S. Khaksar, A. Heydari, M. Tajbakhsh, and S.M. Vahdat J. Fluorine Chem. 131 2010 1377 1381
61. S. Khaksar, and M. Alipour Monatsh. Chem. 144 2013 395 398
62. R. Chebolu, D.N. Kommi, D. Kumar, N. Bollineni, and A.K. Chakraborti J. Org. Chem. 77 2012 10158 10167
63. J. Elguero, P. Goya, N. Jagerovic, and A.M.S. Silva Targets Heterocycl. Syst. 6 2002 52 98
64. N.K. Terrett, A.S. Bell, D. Brown, and P. Ellis Bioorg. Med. Chem. Lett. 6 1996 1819 1824
65. K.Y. Lee, J.M. Kim, and J.N. Kim Tetrahedron Lett. 44 2003 6737 6740
66. N. Haddad, and J. Baron Tetrahedron Lett. 43 2002 2171 2173
67. J. Bohrisch, M. Patzel, C. Mugge, and J. Liebscher Synthesis 1991 1153 1156
68. Y.R. Huang, and J.A. Katzenellenbogen Org. Lett. 2 2000 2833 2836
69. Z.X. Wang, and H.L. Qin Green Chem. 6 2004 90 92
70. K.N. Zelenin Org. Prep. Proced. Int. 27 1995 521 540
71. K. Tkagi, and M. Hubert-Habart J. Heterocycl. Chem. 33 1996 1003 1008
72. R. Oliver, R. SanMartin, and E. Dominguez J. Org. Chem. 65 2000 7010 7019
73. S.L.J. Kennedy Synlett 2008 600 604
74. D. Kralj, M. Friedrich, U. Groselj, S. Kiraly-Potpara, A. Meden, J. Wagger, G. Dahmann, B. Stanovnik, and J. Svete Tetrahedron 65 2009 7151 7162
75. H. Alinezhad, M. Tajbakhsh, and M. Zare J. Fluorine Chem. 132 2011 995 1000
76. S. Fustero, R. Román, J.F. Sanz-Cervera, A. Simón-Fuentes, A.C. Cuňat, S. Villanova, and M. Murguía J. Org. Chem. 73 2008 3523 3529
77. K. Miura, Y. Nishikimi, WO/2008/153027, 2008.
78. H. Enderle, WO/2008/113452, 2008.
79. Y.-J. Hu, M. Tomaszewski, C. Walpole, WO/2005/075476, 2005.
80. G. Jones A.R. Katritzky, A.R. Rees, Comprehensive Heterocyclic Chemistry vol. 2 1984 Pergamon New York, NY 395 (Part 2A)
81. B.K. Chan, and M.A. Ciufolini J. Org. Chem. 72 2007 8489 8495
82. R. Zong, H. Zhou, and R.P. Thummel J. Org. Chem. 73 2008 4334 4337
83. D.A. Powell, and R.A. Batey Org. Lett. 4 2002 2913 2916
84. Z. Liang, and J. Wu Adv. Synth. Catal. 349 2007 1047 1051
85. M. Tokunaga, M. Eckert, and Y. Wakatsuki Angew. Chem., Int. Ed. 38 1999 3222 3225
86. R.P. Korivi, and C. Cheng J. Org. Chem. 71 2006 7079 7082
87. M.V. Spanedda, V.D. Hoang, B. Crousse, D. Bonnet-Delpon, and J.P. Bégué Tetrahedron Lett. 44 2003 217 219
88. A. Saito, J. Kasai, T. Konishi, and Y. Hanzawa J. Org. Chem. 75 2010 6980 6982
89. L.-N. Wang, S.-L. Shen, and J. Qu RSC Adv. 4 2014 30733 30741
90. H.L. Yale, and M. Kalkstein J. Med. Chem. 10 1967 334 336
91. G.L. Neil, L.H. Li, H.H. Buskirk, and T.E. Moxley Cancer Chemother. Rep. 56 1972 163 173
92. S. Niementowski J. Prakt. Chem. 51 1895 564 572
93. A. Bischler Ber. Dtsch. Chem. Ges. 24 1891 506 508
94. A. Riedel, German Patent 174941, 1905.
95. P. Rani, Archana, V.K. Srivastava, and A. Kumar Indian J. Chem. 41B 2002 2642 2646
96. K. Ozaki, Y. Yamada, T. Oine, T. Ishizuka, and Y. Iwasawa J. Med. Chem. 28 1985 568 576
97. R.Z. Qiao, B.L. Xu, and Y.H. Wang Chinese Chem. Lett. 18 2007 656 658
98. S. Khaksar, and S.M. Talesh C.R. Chim. 15 2012 779 783
99. A. Hantzsch Justus Liebigs Ann. Chem. 215 1882 1 82
100. P.P. Mager, R.A. Coburn, A.J. Solo, D.J. Triggle, and H. Rothe Drug Des. Discov. 8 1992 273 289
101. F. Bossert, H. Meyer, and E. Wehinger Angew. Chem., Int. Ed. Engl. 20 1981 762 769
102. H. Nakayama, and Y. Kasoaka Heterocycles 42 1996 901 909
103. A. Heydari, S. Khaksar, M. Tajbakhsh, and H.R. Bijanzadeh J. Fluorine Chem. 130 2009 609 614
104. S. Khaksar, and M. Gholami J. Mol. Liq. 196 2014 159 162
105. C.W. Lindsley, Z. Zhao, W.H. Leister, R.G. Robinson, S.F. Barnett, D. Defeo-Jones, R.E. Jones, G.D. Hartman, J.R. Huff, H.E. Huber, and M.E. Duggan Bioorg. Med. Chem. Lett. 15 2005 761 764
106. M. Loriga, S. Piras, P. Sanna, and G. Paglietti Farmaco 52 1997 157 166
107. L.E. Seitz, W.J. Suling, and R.C. Reynolds J. Med. Chem. 45 2002 5604 5606
108. W. He, M.R. Meyers, B. Hanney, A. Spada, G. Blider, H. Galzeinski, D. Amin, S. Needle, K. Page, Z. Jayyosi, and H. Perrone Bioorg. Med. Chem. Lett. 13 2003 3097 3100
109. Y.B. Kim, Y.H. Kim, J.Y. Park, and S.K. Kim Bioorg. Med. Chem. Lett. 14 2004 541 544
110. S. Khaksar, and F. Rostamnezhad Bull. Korean Chem. Soc. 33 2012 2581 2584
111. T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, H. Kadono, T. Masuda, M. Shimazaki, T. Shintani, K. Fuchikami, K. Sakai, H. Inbe, K. Takeshita, T. Niki, M. Umeda, K.B. Bacon, K.B. Ziegelbauer, and T.B. Lowinger Bioorg. Med. Chem. Lett. 13 2003 913 918
112. M. Mantri, O. De Graaf, J. Van Veldhoven, A. Göblyös, J.K. Von Frijtag Drabbe Künzel, T. Mulder-Krieger, R. Link, H. De Vries, M.W. Beukers, J. Brussee, and A.P. Ijzerman J. Med. Chem. 51 2008 4449 4455
113. J. Deng, T. Sanchez, L.Q. Al-Mawsawi, R. Dayam, R.A. Yunes, A. Garofalo, M.B. Bolger, and N. Neamati Bioorg. Med. Chem. 15 2007 4985 5002
114. S. Khaksar, and M. Yaghoobi J. Fluorine Chem. 142 2012 41 44
115. M. Daryabari, and S. Khaksar J. Mol. Liq. 198 2014 263 266
116. I.E. Soria-Mercado, A. Prieto-Davo, P.R. Jensen, and W.J. Fenical Nat. Prod. 68 2005 904 910
117. K.C. Nicolaou, J.A. Pfefferkorn, and G.Q. Cao Angew. Chem., Int. Ed. 39 2000 734 739
118. Y. Moumou, J. Vasseur, F. Trotin, and J. Dubois Phytochemical 62 1992 265 278
119. G.-X. Li, and J. Qu Chem. Commun. 46 2010 2653 2655
120. S. Khaksar, A. Rouhollahpour, and S.M. Talesh J. Fluorine Chem. 141 2012 11 15
121. T. Eicher, S. Hauptmann, and A. Speicher The Chemistry of Heterocycles 2003 Wiley-VCH New York, NY (Chapter 5, Section 5.6)
122. N. Fokialakis, C.L. Cantrell, S.O. Duke, A.L.S. Kaltsounis, and A.E. Wedge J. Agric. Food Chem. 54 2006 1651 1655
123. K. Gewald, E. Schinke, and H. Bottcher Chem. Ber. 99 1966 94 100
124. K. Gewald Angew. Chem. 73 1961 114 118
125. L. Knorr Ber. Dtsch. Chem. Ges. 18 1885 299 311
126. C. Paal Ber. Dtsch. Chem. Ges. 18 1885 367 371
127. C. Paal Ber. Dtsch. Chem. Ges. 18 1885 2251 2254
128. H. Fiesselmann, and P. Schipprak Chem. Ber. 87 1954 835 841
129. L.-R. Wen, T. He, M.-C. Lan, and M. Li J. Org. Chem. 78 2013 10617 10628
130. Q. He, X. Zhu, M. Shi, M. Zhao, J. Zhao, S. Zhang, and J. Miao Bioorg. Med. Chem. 15 2007 3889 3895
131. V. Raparti, T. Chitre, K. Bothara, V. Kumar, S. Dangre, C. Khachane, S. Gore, and B. Deshmane Eur. J. Med. Chem. 44 2009 3954 3960
132. A. Arcelli, D. Balducci, S.D.F.E. Neto, G. Porzi, and M. Sandri Tetrahedron: Asymmetry 18 2007 562 568
133. D. Zhu, R. Chen, H. Liang, S. Li, L. Pan, and X. Chen Synlett 2010 897 900