Regioselective rapid analog synthesis of 1,3-(or 1,5-)diphenyl-4-aryl/ heteroaryl-5-(or 3-)(methylthio)pyrazoles via Suzuki cross-coupling

Tetrahedron

Volumn 67, Issue 16, 2011, Pages 2961-2968

  Khan, Taukeer A ^a   Kumar, Sarvesh ^a   Venkatesh, Chelvam ^a   Ila, Hiriyakkanavar ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

Halogenation; Pyrazole; Regioselective; Suzuki coupling

Indexed keywords

3 (METHYLTHIO) 1,4,5 TRIPHENYL 1H PYRAZOLE; 3 (METHYLTHIO) 1,5 DIPHENYL 4 (THIOPHEN 2 YL) 1H PYRAZOLE; 3 (METHYLTHIO) 1,5 DIPHENYL 4 PHENYLETHYNYL 1H PRAZOLE; 4 (1 BENZENESULFONYL 1H INDOL 3 YL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (1 BENZENESULFONYL 1H INDOL 3 YL) 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 4 (1 METHYL 1H INDOL 5 YL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (1 METHYL 1H INDOL 5 YL) 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 4 (2 FURYL) 1,5 DIPHENYL 1H PYRAZOLE; 4 (4 ACETYLPHENYL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (4 ACETYLPHENYL) 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 4 (4 METHOXYPHENYL) 1,3 DIPHENYL 1H PRAZOLE; 4 (4 METHOXYPHENYL) 1,5 DIPHENYL 1H PRAZOLE; 4 (4 METHOXYPHENYL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (4 METHOXYPHENYL) 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 4 (BENZOFURAN 2 YL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (BENZOFURAN 2 YL) 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 4 (FURAN 2 YL) 1,3 DIPHENYL 1H PRAZOLE; 4 (FURAN 2 YL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (FURAN 2 YL) 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 4 (PYRIDIN 3 YL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (QUINOLIN 3 YL) 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 (QUINOLIN 3 YL) 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 4 BROMO 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 IODO 3 (METHYLTHIO) 1,5 DIPHENYL 1H PYRAZOLE; 4 IODO 5 (METHYLTHIO) 1,3 DIPHENYL 1H PYRAZOLE; 5 (METHYLTHIO) 1,3 DIPHENYL 4 (THIOPHEN 2 YL) 1H PYRAZOLE; 5 (METHYLTHIO) 1,3 DIPHENYL 4 PHENYLETHYNYL 1H PRAZOLE; 5 (METHYLTHIO) 1,3,4 TRIPHENYL 1H PYRAZOLE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HALOGENATION; PRIORITY JOURNAL; SUZUKI REACTION;

EID: 79953196824     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.02.043     Document Type: Article

References (84)

1. Reviews:
2. J. Elguero A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 5 1984 Pergamon Oxford 273 291
3. J. Elguero I. Shinkai, Comprehensive Heterocyclic Chemistry Vol. 3 1996 Pergamon Oxford 3 75
4. J. Elguero, P. Goya, N. Jagerovic, and A.M.S. Silva O.A. Attanasi, D. Spinelli, Pyrazoles as Drugs: Facts and Fantasies in Targets in Heterocyclic Systems Vol. 6 2002 Italian Society of Chemistry Roma 52 98 and references therein
5. P. Singh, K. Paul, and W. Holzer Bioorg. Med. Chem. 14 2006 5061 and references therein
6. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson J. Med. Chem. 40 1997 1347
7. N.K. Terrett, A.S. Bell, D. Brown, and P. Ellis Bioorg. Med. Chem. Lett. 6 1996 1819
8. A.A. Bekhit, and T. Abdel-Aziem Bioorg. Med. Chem. 12 2004 1935
9. C. Selvam, S.M. Jachak, P. Thilagavathi, and A.A. Chakraborti Bioorg. Med. Chem. Lett. 15 2005 1793
10. Z. Sui, J. Guan, M.P. Ferro, K. McCoy, M.P. Wachter, W.V. Murray, M. Singer, M. Steber, D.M. Ritchie, and D.C. Argentieri Bioorg. Med. Chem. Lett. 10 2000 601
11. S.R. Stauffer, C.J. Coletta, R. Tedesco, G. Nishiguchi, K. Carlson, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen J. Med. Chem. 43 2000 4934
12. S.R. Stauffer, Y. Huang, C.J. Coletta, R. Tedesco, and J.A. Katzenellenbogen Bioorg. Med. Chem. 9 2001 141
13. S.R. Stauffer, and J.A. Katzenellenbogen J. Comb. Chem. 2 2000 318
14. A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, K. Suzuki, T. Ueda, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi, and J.-I. Yamagishi Bioorg. Med. Chem. 12 2004 5515
15. R. Katoch-Rouse, O.A. Pavlova, T. Caulder, A.F. Hoffman, A.G. Mukhin, and A.G. Horti J. Med. Chem. 46 2003 642
16. K.W. Moore, K. Bonner, E.A. Jones, F. Emms, P.D. Leeson, R. Marwood, S. Patel, S. Patel, M. Rowley, S. Thomas, and R.W. Carling Bioorg. Med. Chem. Lett. 9 1999 1285
17. J. Zhang, S. Didierlaurent, M. Fortin, D. Lefrancois, E. Uridat, and J.P. Vevert Bioorg. Med. Chem. Lett. 10 2000 2575
18. Wu, T.T.; Scribner, A.W. WO Patent 0164651, 2001.
19. Chem. Abstr. 135 2001 226990
20. Luethy, C.; Nebel, K.; Wenger, J. WO Patent 0130782, 2001.
21. Chem. Abstr. 134 2001 340513
22. S.K. Singh, M.S. Reddy, S. Shivaramakrishna, D. Kavitha, R. Vasudev, J.M. Babu, A. Sivalakshmidevi, and Y.K. Rao Tetrahedron Lett. 45 2004 7679
23. K.Y. Lee, J.M. Kim, and J.N. Kim Tetrahedron Lett. 44 2003 6737
24. D.B. Grotjahn, S. Van, D. Combs, D.A. Lev, C. Schneider, M. Rideout, C. Meyer, G. Hernandez, and L. Mejorado J. Org. Chem. 67 2002 9200
25. N. Haddad, and J. Baron Tetrahedron Lett. 43 2002 2171
26. V. Molteni, M.M. Hamilton, L. Mao, C.M. Crane, A.P. Termin, and D.M. Wilson Synthesis 2002 1669
27. A.R. Katritzky, M. Wang, S. Zhang, and M.V. Voronkov J. Org. Chem. 66 2001 6787
28. Y.R. Huang, and J.A. Katzenellenbogen Org. Lett. 2 2000 2833
29. A.R. Katritzky, A. Denisenko, S.N. Denisenko, and M. Arend J. Heterocycl. Chem. 37 2000 1309
30. T.L. Gilchrist Heterocyclic Chemistry 3rd ed. 1997 Longman Essex England
31. T. Norris, R. Colon-Cruz, and D.H.B. Ripin Org. Biomol. Chem. 3 2005 1844
32. B.C. Bishop, K.M.J. Brands, A.D. Gibb, and D.J. Kennedy Synthesis 2004 43
33. R.D. Miller, and O. Reiser J. Heterocycl. Chem. 30 1993 755
34. M.V. Patel, R. Bell, S. Majest, R. Henry, and T. Kolasa J. Org. Chem. 69 2004 7058
35. S.M. Sakya, and B. Rast Tetrahedron Lett. 44 2003 7629
36. J.J. Neumann, M. Suri, and F. Glorius Angew. Chem., Int. Ed. 49 2010 7790
37. S. Majumder, K.R. Gipson, R.J. Staples, and A.L. Odom Adv. Synth. Catal. 351 2009 2013
38. Lack of regioselectivity:
39. V.L.M. Silva, A.M.S. Silva, D.C.G.A. Pinto, J.A.S. Cavaleiro, and J. Elguero Eur. J. Org. Chem. 2004 4348
40. S.T. Heller, and S.R. Natarajan Org. Lett. 8 2006 2675
41. A.C. Spivey, C.M. Diaper, H. Adams, and A.J. Rudge J. Org. Chem. 65 2000 5253
42. C. Kashima, H. Harada, I. Kita, I. Fukuchi, and A. Hosomi Synthesis 1994 61
43. A. Padwa 1,3-Dipolar Cycloaddition Chemistry Vol. 1 1984 John Wiley New York, NY
44. V.K. Aggarwal, J. de Vicente, and R.V. Bonnert J. Org. Chem. 68 2003 5381
45. Review on general method of synthesis of pyrazoles (both 1,3-dicarbonyl compounds and dipolar cycloaddition) B. Stanovnik, J.D. Svete, Science of Synthesis Vol. 12 2002 Thieme Stuttgart 22 81 pp 84-91
46. A. Padwa, W.H. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products 2002 John Wiley New York, NY
47. X. Deng, and N.S. Mani Org. Lett. 10 2008 1307
48. X. Deng, and N.S. Mani J. Org. Chem. 73 2008 2412 and references therein
49. T.D. Penning, S.W. Kramer, L.F. Lee, P.W. Collins, C.M. Koboldt, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson Bioorg. Med. Chem. Lett. 7 1997 2121
50. S. Peruncheralathan, T.A. Khan, H. Ila, and H. Junjappa J. Org. Chem. 70 2005 10030
51. Review:
52. F. Alonso, I.P. Beletskaya, and M. Yus Tetrahedron 64 2008 3047
53. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
54. S.P. Stanforth Tetrahedron 54 1998 263
55. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633
56. A. Suzuki D.G. Hall, Boronic Acids 2005 Wiley-VCH Weinheim, Germany 123 170 Chapter 3
57. N. Miyaura Metal-Catalyzed Cross Coupling Reactions 2004 Wiley-VCH Weinheim, Germany Chapter 2
58. I.J.S. Fairlamb Chem. Soc. Rev. 36 2007 1036
59. F. Bellina, A. Carpita, and R. Rossi Synthesis 2004 2419
60. N. Miyaura Top. Curr. Chem. 219 2002 11
61. A. Suzuki J. Organomet. Chem. 576 1999 147
62. A.M. Rouhi Chem. Eng. News 82 2004 49
63. J.S. Carey, D. Laffan, C. Thomson, and M.T. Williams Org. Biomol. Chem. 4 2006 2337
64. T. Delaunay, P. Genix, M. Es-Sayed, J.-P. Vors, N. Monteiro, and G. Balme Org. Lett. 12 2010 3328
65. B. Cottineau, and J. Chenault Synlett 2002 769
66. S. Beltrán-Rodil, M.G. Edwards, D.S. Pugh, M. Reid, and R.J.K. Taylor Synlett 2010 602
67. S. Guillou, O. Nesmes, M.S. Ermolenko, and Y.L. Janin Tetrahedron 65 2009 3529
68. C.A. Dvorak, D.A. Rudolph, S. Ma, and N.I. Carruthers J. Org. Chem. 70 2005 4188
69. P.S. Dragovich, T.M. Bertolini, B.K. Ayida, L.-S. Li, D.E. Murphy, F. Ruebsam, Z. Sun, and Y. Zhou Tetrahedron 63 2007 1154
70. S. Bourrain, M. Ridgill, and I. Collins Synlett 2004 795
71. A.-L. Gérard, C. Mahatsekake, V. Collot, and S. Rault Tetrahedron Lett. 48 2007 4123
72. M. McLaughlin, K. Marcantonio, C.-Y. Chen, and I.W. Davies J. Org. Chem. 73 2008 4309
73. D.L. Browne, M.D. Helm, A. Plant, and J.P.A. Harrity Angew. Chem., Int. Ed. 46 2007 8656
74. N. Kudo, M. Perseghini, and G.C. Fu Angew. Chem., Int. Ed. 45 2006 1282
75. K.M. Clapham, A.S. Batsanov, M.R. Bryce, and B. Tarbit Org. Biomol. Chem. 7 2009 2155
76. 4 to 5 mol % in the cross-coupling of 5a with boronic acid 11a resulted in lower yield of 7a (52%) under similar reaction conditions.
77. 2, chemical formula weight 348.49, monoclinic, unit cell parameters: a=5.722 (2), b=8.231 (3), c=17.850 (7), α=90, β=99.192 (7), γ=90, space group P1c1. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.Uk ).
78. M.A. Kira, M.O. Abdel-Rahman, and K.Z. Gadalla Tetrahedron Lett. 1969 109
79. T. De Paulis, K. Hemstapat, Y. Chen, Y. Zhang, S. Saleh, D. Alagille, R.M. Baldwin, G.D. Tamagnan, and P.J. Conn J. Med. Chem. 49 2006 3332
80. I.R. Robertson, and J.T. Sharp Tetrahedron 40 1984 3095
81. L.M. Subramanian, and G.S. Misra Synthesis 1984 1063
82. L. Muthusubramanian, and G.S. Misra Eur. J. Med. Chem. 21 1986 163
83. K. Singh, P.K. Sharma, S.N. Dhawan, and S.P. Singh J. Chem. Res. 2005 526
84. O. Prakash, D. Sharma, R. Kamal, R. Kumar, and R.R. Nair Tetrahedron 65 2009 10175