Reactions of vinyl sulfone with α-diazo-β-ketosulfone and Bestmann-Ohira reagent for the regioselective synthesis of highly functionalized pyrazoles

Tetrahedron

Volumn 70, Issue 9, 2014, Pages 1794-1799

  Kumar, Rahul ^a   Nair, Deepa ^a   Namboothiri, Irishi N N ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Bestmann Ohira reagent; Diazosulfone; Pyrazoles; vinyl sulfone

Indexed keywords

ALPHA DIAZO BETA KETOSULFONE; BESTMANN OHIRA REAGENT; DIAZOMETHYLPHOSPHONATE; DIAZOMETHYLSULFONE; PHOSPHONYLPYRAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; SILICA GEL; SULFONE DERIVATIVE; SULFONYLPYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VINYL SULFONE;

ARTICLE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CYCLOADDITION; ELIMINATION REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84893769445     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.01.022     Document Type: Article

References (73)

1. J. Elguero A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry Vol. 3 1996 Pergamon Oxford, UK 1
2. A.V. Dolzhenko, A.V. Dolzhenko, and W.K. Chui Heterocycles 75 2008 1575
3. S. Dadiboyena, and A. Nefzi Eur. J. Med. Chem. 46 2011 5258
4. S. Fustero, M. Sanchez-Rosello, P. Barrio, and A. Simon-Fuentes Chem. Rev. 111 2011 6984
5. A. Schmidt, and A. Dreger Curr. Org. Chem. 15 2011 1423
6. J.-Y. Yoon, S. Lee, and H. Shin Curr. Org. Chem. 15 2011 657
7. V. Kumar, K. Kaur, G.K. Gupta, and A.K. Sharma Eur. J. Med. Chem. 69 2013 735
8. C. Lamberth Heterocycles 71 2007 1467
9. D. Secci, A. Bolasco, P. Chimenti, and S. Carradori Curr. Med. Chem. 18 2011 5114
10. 2: D. Verma, R. Kumar, and I.N.N. Namboothiri J. Org. Chem. 78 2013 3482
11. H. Ichikawa, R. Watanabe, Y. Fujino, and Y. Usami Tetrahedron Lett. 52 2011 4448
12. S. Majumder, K.R. Gipson, R.J. Staples, and A.L. Odom Adv. Synth. Catal. 351 2009 2013
13. A.A. Wube, E.-M. Wenzig, S. Gibbons, K. Asres, R. Bauer, and F. Bucar Phytochemistry 69 2008 982
14. S. Fustero, R. Roman, J.F. Sanz-Cervera, A. Simon-Fuentes, A.C. Cunat, S. Villanova, and M. Murguia J. Org. Chem. 73 2008 3523
15. S. Fustero, R. Roman, J.F. Sanz-Cervera, A. Simon-Fuentes, J. Bueno, and S. Villanova J. Org. Chem. 73 2008 8545
16. R. Surmont, G. Verniest, and N. De Kimpe Org. Lett. 12 2010 4648
17. For anti-inflammatory drug Celecoxib: M.A. Chowdhury, K.R.A. Abdellatif, Y. Dong, G. Yu, Z. Huang, M. Rahman, D. Das, C.A. Velazquez, M.R. Suresh, and E.E. Knaus Bioorg. Med. Chem. Lett. 20 2010 1324
18. For synthesis of Withasomnine from nitroalkene and diazosulfone: R. Kumar, and I.N.N. Namboothiri Org. Lett. 13 2011 4016 and the references cited therein
19. M. Viciano-Chumillas, S. Tanase, L.J. De Jongh, and J. Reedijk Eur. J. Inorg. Chem. 2010 3403
20. M.A. Halcrow Dalton Trans. 2009 2059
21. S.O. Ojwach, and J. Darkwa Inorg. Chim. Acta 363 2010 1947
22. J. Perez, and L. Riera Eur. J. Inorg. Chem. 2009 4913
23. A. Schmidt, and A. Dreger Curr. Org. Chem. 15 2011 2897
24. J. Elguero, C. Marzin, P. Linda, and A.R. Katritzky The Tautomerism of Heterocycles 1976 Academic New York, NY 655
25. P. Cornago, P. Cabildo, R.M. Claramunt, L. Bouissane, E. Pinilla, M.R. Torres, and J. Elguero New J. Chem. 33 2009 125 and the references cited therein
26. F. Palacios, C. Alonso, and J.M. de los Santos Chem. Rev. 105 2005 899
27. B. Lejczak, and P. Kafarski Top. Heterocycl. Chem. 20 2009 31
28. M. Syamala Org. Prep. Proced. Int. 37 2005 103
29. K. Bera, D. Nadkarni, and I.N.N. Namboothiri J. Chem. Sci. 125 2013 443
30. T.G. Back, K.N. Clary, and D. Gao Chem. Rev. 110 2010 4498
31. A. El-Awa, M.N. Noshi, X.M.D. Jourdin, and P.L. Fuchs Chem. Rev. 109 2009 2315
32. D.A. Alonso, and C. Najera Org. React. 72 2008 367
33. E.N. Prilezhaeva Russ. Chem. Rev. 69 2000 367
34. G. Molteni ARKIVOC 2007 224
35. M. Regitz, and H. Heydt A. Padwa, 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley Interscience New York, NY Chapter 4
36. G.K. Trivedi J. Indian Chem. Soc. 81 2004 187
37. H. Zollinger Diazo Chemistry II-Aliphatic, Inorganic and Organometallic Compounds 1995 VCH Weinheim, Germany 11
38. F. Diederrich, L. Isaacs, and D. Philip Chem. Soc. Rev. 23 1994 243
39. R.J. Mullins J.J. Li, Name Reactions in Heterocyclic Chemistry II 2011 John Wiley & Sons Hoboken, New Jersey 327
40. K. Harju, and J. Yli-Kauhaluoma P.H. Toy, Y. Lam, Solid-phase Organic Synthesis 2012 John Wiley & Sons Hoboken, New Jersey 355
41. V. Kumar, R. Aggarwal, and S.P. Singh Heterocycles 75 2008 2893
42. J. Kempson J.J. Li, Name Reactions in Heterocyclic Chemistry II 2011 John Wiley & Sons Hoboken, New Jersey 317
43. R. Lu, and H. Yang Tetrahedron Lett. 38 1997 5201
44. Y. Shen, J. Zheng, Y. Xin, Y. Lin, and M. Qi J. Chem. Soc., Perkin Trans. 1 1995 997
45. E. Budzisz, M. Malecka, and B. Nawrot Tetrahedron 60 2004 1749
46. A. Padwa, and W.M. Wannamaker Tetrahedron 46 1990 1145
47. D. Gao, H. Zhai, M. Parvez, and T.G. Back J. Org. Chem. 73 2008 8057
48. M.M. Savant, M.A. Pansuriya, V.C. Bhuva, N. Kapuriya, N.A. Patel, B.V. Audichya, V.P. Pipaliya, and T.Y. Naliapara J. Comb. Chem. 12 2010 176
49. S.O. Kanishchev, P.Y. Bandera, M.V. Timoshenko, B.E. Rusanov, S.A. But, and G.Y. Shermolovich Chem. Heterocycl. Compd. 43 2007 887
50. P. Meffre, S. Hermann, P. Durand, G. Reginato, and A. Riu Tetrahedron 58 2002 5159 and the references cited therein
51. R. Muruganantham, S.M. Mobin, and I.N.N. Namboothiri Org. Lett. 9 2007 1125
52. R. Muruganantham, and I.N.N. Namboothiri J. Org. Chem. 75 2010 2197
53. In situ generated acrylo- and alkylidenemalononitrile: K. Mohanan, A.R. Martin, L. Toupet, M. Smietana, and J. Vasseur Angew. Chem., Int. Ed. 49 2010 3196
54. D. Verma, S.M. Mobin, and I.N.N. Namboothiri J. Org. Chem. 76 2011 4764
55. In situ generated enone: A.R. Martin, K. Mohanan, L. Toupet, J.J. Vasseur, and M. Smietana Eur. J. Org. Chem. 2011 3184
56. R. Kumar, D. Verma, S.M. Mobin, and I.N.N. Namboothiri Org. Lett. 14 2012 4070
57. K. Doyle, and C. Moody Tetrahedron 50 1994 3761 and the references cited therein
58. R. Tanikaga, T. Tamura, Y. Nozaki, and A. Kaji J. Chem. Soc., Chem. Commun. 1984 87
59. T. Nakata Chem. Soc. Rev. 39 2010 1955
60. Q. Zhu, and Y. Lu Aust. J. Chem. 62 2009 951
61. T. Pathak Tetrahedron 64 2008 3605
62. A.B. Charette, A. Cote, J.-N. Desrosiers, I. Bonnaventure, V.N.G. Lindsay, C. Lauzon, J. Tannous, and A.A. Boezio Pure Appl. Chem. 80 2008 881
63. N. Ono Heterocycles 75 2008 243
64. S.B. Tsogoeva Eur. J. Org. Chem. 2007 1701
65. D.C. Meadows, and J. Gervay-Hague Med. Res. Rev. 26 2006 793
66. M. Flores, P. Garcia-Garcia, N.M. Garrido, I.S. Marcos, F. Sanz-Gonzalez, and D. Diez J. Org. Chem. 78 2013 7068
67. L. Guideri, F. De Sarlo, and F. Machetti Chem. - Eur. J. 19 2013 665
68. J. Hernandez-Toribio, S. Padilla, J. Adrio, and J.C. Carretero Angew. Chem., Int. Ed. 51 2012 8854
69. S. Dey, D. Datta, and T. Pathak Synlett 2011 2521
70. C.S. Shanahan, N.O. Fuller, B. Ludolph, and S.F. Martin Tetrahedron Lett. 52 2011 4076
71. I. Coldham, A.J.M. Burrell, H.D.S. Guerrand, and N. Oram Org. Lett. 13 2011 1267
72. J.S. Meek, and J.S. Fowler J. Org. Chem. 33 1968 985
73. S.B. Nosachev, N.A. Shchurova, E.A. Tyrkova, and A.G. Tyrkov Russ. J. Org. Chem. 45 2009 463