Selective sequential cross-coupling reactions on imidazole towards neurodazine and analogues

Synthesis (Germany)

Volumn 45, Issue 10, 2013, Pages 1387-1405

  Recnik, Lisa Maria ^a   Abd El Hameid, Mohammed ^b   Haider, Maximilian ^a   Schnürch, Michael ^a   Mihovilovic, Marko D ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^b CAIRO UNIVERSITY   (Egypt)

Author keywords

cross coupling; heterocycles; homogeneous catalysis; palladium; regioselectivity

Indexed keywords

BIOACTIVE MOLECULES; BIOLOGICALLY ACTIVE MOLECULES; CROSS-COUPLINGS; FLEXIBLE STRATEGIES; HETEROCYCLES; HOMOGENEOUS CATALYSIS; SEQUENTIAL CROSS-COUPLING REACTIONS; SUZUKI-MIYAURA CROSS-COUPLING;

PALLADIUM; REACTION KINETICS; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

PLANTS (BOTANY);

1 BENZYL 2 (2 FURYL) 4,5 DI(4 METHOXYPHENYL) 1H IMIDAZOLE; 1 BENZYL 2 (3 NITROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 1 BENZYL 2 (4 NITROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 1 BENZYL 2,4,5 TRIBROMO 1H IMIDAZOLE; 1 BENZYL 2,4,5 TRIPHENYL 1H IMIDAZOLE; 1 BENZYL 4,5 DI(3 NITROPHENYL) 2 (2 TOLYL) 1H IMIDAZOLE; 1 BENZYL 4,5 DI(4 METHOXYPHENYL) 2 (2 TOLYL) 1H IMIDAZOLE; 1 BENZYL 4,5 DIBROMO 2 (2 FURYL) 1H IMIDAZOLE; 1 BENZYL 4,5 DIBROMO 2 (2 TOLYL) 1H IMIDAZOLE; 1 BENZYL 4,5 DIBROMO 2 (3 NITROPHENYL) 1H IMIDAZOLE; 1 BENZYL 4,5 DIBROMO 2 (4 NITROPHENYL) 1H IMIDAZOLE; 1 BENZYL 4,5 DIBROMO 2 PHENYL 1H IMIDAZOLE; 2 (4 METHOXYPHENYL) 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 4,5 DIPHENYL 1H IMIDAZOLE; 2,4,5 TRIBROMO 1 (4 METHOXYBENZYL) 1H IMIDAZOLE; 2,4,5 TRIBROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 1H IMIDAZOLE; 4,5 DIBROMO 1 (4 METHOXYBENZYL) 2 PHENYL 1H IMIDAZOLE; 4,5 DIBROMO 1 (4 METHOXYPHENYL) 2 (2 TOLYL) 1H IMIDAZOLE; 4,5 DIBROMO 1 (4 METHOXYPHENYL) 2 (3 NITROPHENYL) 1H IMIDAZOLE; 4,5 DIBROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 2 (2 TOLYL) 1H IMIDAZOLE; 4,5 DIBROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 2 (3 NITROPHENYL) 1H IMIDAZOLE; 4,5 DIBROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 2 (4 NITROPHENYL) 1H IMIDAZOLE; 4,5 DIBROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 2 PHENYL 1H IMIDAZOLE; 4,5 DIBROMO 2 (2 FURYL) 1 (4 METHOXYPHENYL) 1H IMIDAZOLE; 4,5 DIBROMO 2 (2 FURYL) 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 1H IMIDAZOLE; 4,5 DIBROMO 2 (4 METHOXYPHENYL) 1 (4 METHOXYBENZYL) 1H IMIDAZOLE; 4,5 DIBROMO 2 (4 METHOXYPHENYL) 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 1H IMIDAZOLE; BORONIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; NEURODAZINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ARTICLE; ARYLATION; CATALYSIS; CELL DIFFERENTIATION; CELL TRANSFORMATION; CHROMATOGRAPHY; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; ELECTROPHILICITY; MOUSE; NERVE CELL; NONHUMAN; PLURIPOTENT STEM CELL; STRUCTURE ACTIVITY RELATION; SUZUKI REACTION;

EID: 84877585698     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316906     Document Type: Article

References (77)

1. Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N. Beilstein J. Org. Chem. 2011, 7, 442.
2. Kosjek, T.; Heath, E. Top. Heterocycl. Chem. 2012, 27, 219.
3. Bellus, D. Lect. Heterocycl. Chem. 1987, 9, 65.
4. Beier, C.; Benting, J.; Coqueron, P.-Y.; Dunkel, R.; Greul, J.; Grosjean-Cournoyer, M.-C.; Hadano, H.; Rinolfi, P.; Vors, J.-P. PCT Int. Appl WO 2010055114 A1 20100520, 2010; Chem. Abstr. 2010, 152, 592056.
5. Dumeunier, R.; Lamberth, C.; Trah, S.; Wendeborn, S. PCT Int. Appl WO 2009053102 A1 20090430, 2009; Chem. Abstr. 2009, 150, 494866.
6. Muller, T.; Braese, S. Angew. Chem. Int. Ed. 2011, 50, 11844.
7. Rasmussen, S. C.; Schwiderski, R. L.; Mulholland, M. E. Chem. Commun. 2011, 47, 11394.
8. Maly, K. E. J. Mater. Chem. 2009, 19, 1781.
9. Elbing, M.; Bazan, G. C. Angew. Chem. Int. Ed. 2008, 47, 834.
10. Jin, Z. Nat. Prod. Rep. 2011, 28, 1143.
11. Koswatta, P. B.; Lovely, C. J. Nat. Prod. Rep. 2011, 28, 511.
12. Sawaya, A. C. H. F.; Abreu, I. N.; Andreazza, N. L.; Eberlin, M. N.; Mazzafera, P. In Alkaloids: Properties, Application and Pharmacological Effects; Cassiano, N. M., Ed.; Nova Science Publishers Inc.: Hauppauge N.Y., 2010, 63-80.
13. Boehm, J. C.; Smietana, J. M.; Sorenson, M. E.; Garigipati, R. S.; Gallagher, T. F.; Sheldrake, P. L.; Bradbeer, J.; Badger, A. M.; Laydon, J. T.; Lee, J. C.; Hillegass, L. M.; Griswold, D. E.; Breton, J. J.; Chabot- Fletcher, M. C.; Adams, J. L. J. Med. Chem. 1996, 39, 3929.
14. Biradar, J. S.; Mugali, P. S.; Somappa, S. B.; Rajesab, P. Org. Chem. Indian J. 2008, 4, 408.
15. Williams, D. R.; Lee, M.-R.; Song, Y.-A.; Ko, S.-K.; Kim, G.-H.; Shin, I. J. Am. Chem. Soc. 2007, 129, 9258.
16. Williams, D. R.; Kim, G.-H.; Lee, M.-R.; Shin, I. Nat. Protoc. 2008, 3, 835.
17. Shin, I.-J.; Lee, M.-R.; Williams, D. PCT Int. Appl WO 2007061153 A1 20070531, 2007; Chem. Abstr. 2007, 147, 9916.
18. Takahashi, K.; Yamanaka, S. Cell 2006, 126, 663.
19. Maherali, N.; Hochedlinger, K. Cell Stem Cell 2008, 3, 595.
20. Lowry, W. E.; Richter, L.; Yachechko, R.; Pyle, A. D.; Tchieu, J.; Sridharan, R.; Clark, A. T.; Plath, K. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2883.
21. Park, I. H.; Zhao, R.; West, J. A.; Yabuuchi, A.; Huo, H.; Ince, T. A.; Lerou, P. H.; Lensch, M. W.; Daley, G. Q. Nature 2008, 451, 141.
22. Takahashi, K.; Tanabe, K.; Ohnuki, M.; Narita, M.; Ichisaka, T.; Tomoda, K.; Yamanaka, S. Cell 2007, 131, 861.
23. Yu, J.; Vodyanik, M. A.; Smuga-Otto, K.; Antosiewicz-Bourget, J.; Frane, J. L.; Tian, S.; Nie, J.; Jonsdottir, G. A.; Ruotti, V.; Stewart, R.; Slukvin, I. I.; Thomson, J. A. Science 2007, 318, 1917.
24. For reviews, see: Zhu, S.; Wurdak, H.; Schultz, P. G. Future Med. Chem. 2010, 2, 965.
25. Lyssiotis, C. A.; Lairson, L. L.; Boitano, A. E.; Wurdak, H.; Zhu, S.; Schultz, P. G. Angew. Chem. Int. Ed. 2011, 50, 200.
26. Lo, K. W-H.; Ashe, K. M.; Kan, H. M.; Laurencin, C. T. Regener. Med. 2012, 7, 535.
27. Song, H.; Chang, W.; Song, B.-W.; Hwang, K.-C. Am. J. Stem Cells 2012, 1, 22.
28. Andrews, P. D. Future Med. Chem. 2011, 3, 1539.
29. Yuan, X.; Li, W.; Ding, S. Prog. Drug Res. 2011, 67, 253.
30. Lukaszewicz, A. I.; McMillan, M. K.; Kahn, M. J. Med. Chem. 2010, 53, 3439.
31. Li, W.; Ding, S. Trends Pharmacol. Sci. 2010, 31, 36.
32. Grimmett, M. R. In Science of Synthesis; Vol. 12; Neier, R., Ed.; Thieme: Stuttgart, 2002, 325-528.
33. Samai, S.; Nandi, G. C.; Singh, P.; Singh, M. S. Tetrahedron 2009, 65, 10155.
34. Lipshutz, B. H.; Hagen, W. Tetrahedron Lett. 1992, 33, 5865.
35. Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 3283.
36. Schroeter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
37. Wang, J.-R.; Manabe, K. Synthesis 2009, 1405.
38. Djakovitch, L.; Batail, N.; Genelot, M. Molecules 2011, 16, 5241.
39. Slagt, V. F.; de Vries, A. H. M.; de Vries, J. G.; Kellogg, R. M. Org. Process Res. Dev. 2010, 14, 30.
40. Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036.
41. Banwell, M. G.; Goodwin, T. E.; Ng, S.; Smith, J. A.; Wong, D. J. Eur. J. Org. Chem. 2006, 3043.
42. de Meijere, A.; von Zezschwitz, P.; Nuske, H.; Stulgies, B. J. Organomet. Chem. 2002, 653, 129.
43. Dang, T. T.; Dang, T. T.; Rasool, N.; Villinger, A.; Langer, P. Adv. Synth. Catal. 2009, 351, 1595.
44. Neenan, T. X.; Whitesides, G. M. J. Org. Chem. 1988, 53, 2489.
45. Eichhorn, S. H.; Paraskos, A. J.; Kishikawa, K.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 12742.
46. Toguem, S.-M. T.; Villinger, A.; Langer, P. Synlett 2009, 3311.
47. Toguem, S.-M. T.; Villinger, A.; Langer, P. Synlett 2010, 909.
48. Sharif, M.; Zeeshan, M.; Reimann, S.; Villinger, A.; Langer, P. Tetrahedron Lett. 2010, 51, 2810.
49. Akrawi, O. A.; Hussain, M.; Langer, P. Tetrahedron Lett. 2011, 52, 1093.
50. Hussain, M.; Khera, R. A.; Nguyen, T.-H.; Langer, P. Org. Biomol. Chem. 2011, 9, 370.
51. Zinad, D. S.; Feist, H.; Villinger, A.; Langer, P. Tetrahedron 2012, 68, 711.
52. Shibahara, F.; Yamauchi, T.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2012, 77, 8815.
53. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 36, 3437.
54. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
55. Langhammer, I.; Erker, T. Heterocycles 2005, 65, 2721.
56. Skoumbourdis, A. P.; Moore, S.; Landsman, M.; Thomas, C. J. Tetrahedron Lett. 2007, 48, 9140.
57. Strotman, N. A.; Chobanian, H. R.; He, J.; Guo, Y.; Dormer, P. G.; Jones, C. M.; Steves, J. E. J. Org. Chem. 2010, 75, 1733.
58. Kawaski, I.; Yamashita, M.; Ohta, S. Chem. Pharm. Bull. 1996, 44, 1831.
59. Huang, Z.; Jin, J.; Machajewski, T. D.; Antonios-McCrea, W. R.; McKenna, M.; Poon, D.; Renhowe, P. A.; Sendzik, M.; Shafer, C. M.; Smith, A.; Xu, Y.; Zhang, Q. PCT Int. Appl WO 2009115572, 2009; Chem. Abstr. 2009, 151, 403302.
60. Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358.
61. Molander, G. A.; Canturk, B.; Kennedy, L. E. J. Org. Chem. 2009, 74, 973.
62. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley-Interscience: New York, 1999.
63. Felix, A. M.; Heimer, E. P.; Lambros, T. J.; Tzougraki, C.; Meienhofer, J. J. Org. Chem. 1978, 43, 4194.
64. Haddach, A. A.; Kelleman, A.; Deaton-Rewolinski, M. V. Tetrahedron Lett. 2002, 43, 399.
65. Whitten, J. P.; Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1986, 51, 1891.
66. Iddon, B.; Khan, N.; Lim, B. L. J. Chem. Soc., Chem. Commun. 1985, 1428.
67. Langhammer, I.; Erker, T. Heterocycles 2005, 65, 1975.
68. Wang, B.; Sun, H.-X.; Sun, Z.-H.; Lin, G.-Q. Adv. Synth. Catal. 2009, 351, 415.
69. Revesz, L.; Bonne, F.; Makavou, P. Tetrahedron Lett. 1998, 39, 5171.
70. Hasaninejad, A.; Zare, A.; Shekouhy, M.; Ameri Rad, J. J. Comb. Chem. 2010, 12, 844.
71. Ucucu, U.; Karaburun, N. G.; Isikdag, I. Farmaco 2001, 56, 285.
72. Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Tetrahedron 2005, 61, 3539.
73. Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453.
74. Shaabani, A.; Maleki, A.; Behnam, M. Synth. Commun. 2009, 39, 102.
75. Puratchikody, A.; Gopalakrishnan, S.; Nallu, M. Indian J. Pharm. Sci. 2005, 67, 725.
76. Jadhav, S. D.; Kokare, N. D.; Jadhav, S. D. J. Heterocycl. Chem. 2008, 45, 1461.
77. Patel, A.; Bures, F.; Ludwig, M.; Kulhanek, J.; Pytela, O.; Ruzicka, A. Heterocycles 2009, 78, 999.