Synthesis of saturated N-heterocycles

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 2809-2815

  Vo, Cam Van T ^a   Bode, Jeffrey W ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

BIOLOGICALLY ACTIVE MOLECULES; BUILDING BLOCKES; N-HETEROCYCLES;

SCAFFOLDS;

ALDEHYDE DERIVATIVE; CHEMICAL COMPOUND; DIAMINE; ELECTROPHILE; SATURATED N HETEROCYCLE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CROSS COUPLING REACTION; ISOMERIZATION; LITHIATION; NUCLEOPHILICITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84898060409     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5001252     Document Type: Article

References (85)

1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
2. Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; Wiley-VCH Verlag: Weinheim, 2004.
3. Ritchie, T. J.; Macdonald, S. J. F. Drug Discovery Today 2009, 14, 1011
4. Ritchie, T. J.; Macdonald, S. J. F.; Young, R. J.; Pickett, S. D. Drug Discovery Today 2011, 16, 164
5. Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752
6. Leeson, P. D.; St-Gallay, S. A.; Wenlock, M. C. MedChemComm 2011, 2, 91
7. Feher, M.; Schmidt, J. M. J. Chem. Inf. Comput. Sci. 2002, 43, 218
8. Maes, B. W. In Microwave-Assisted Synthesis of Heterocycles; Eycken, E.; Kappe, C. O., Eds.; Springer: Berlin, Heidelberg, 2006; Vol. 1, p 155.
9. Slagt, V. F.; de Vries, A. H. M.; de Vries, J. G.; Kellogg, R. M. Org. Process Res. Dev. 2009, 14, 30
10. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
11. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
12. Eicher, T.; Hauptmann, S.; Speicher, A. Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications; Wiley: Somerset, NJ, 2013.
13. Wolfe, J. P. Synthesis of Heterocycles via Metal-Catalyzed Reactions That Generate One or More Carbon-Heteroatom Bonds; Springer: Berlin, Heidelberg, 2013.
14. Royer, J., Ed. Asymmetric Synthesis of Nitrogen Heterocycles; Wiley-VCH Verlag: Weinheim, 2009.
15. Huang, Y.; Khoury, K.; Dömling, A. In Synthesis of Heterocycles via Multicomponent Reactions I; Orru, R. V. A.; Ruijter, E., Eds.; Springer: Berlin, Heidelberg, 2010; Vol. 23, p 85.
16. Schnurch, M.; Dastbaravardeh, N.; Ghobrial, M.; Mrozek, B.; D. Mihovilovic, M. Curr. Org. Chem. 2011, 15, 2694
17. Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069
18. Mitchell, E. A.; Peschiulli, A.; Lefevre, N.; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2012, 18, 10092
19. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
20. Qin, Y.; Lv, J.; Luo, S. Tetrahedron Lett. 2014, 55, 551
21. Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197
22. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231
23. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552
24. OBrien, P. Chem. Commun. 2008, 655
25. Stead, D.; OBrien, P.; Sanderson, A. Org. Lett. 2008, 10, 1409
26. Bilke, J. L.; Moore, S. P.; OBrien, P.; Gilday, J. Org. Lett. 2009, 11, 1935
27. Bailey, W. F.; Beak, P.; Kerrick, S. T.; Ma, S.; Wiberg, K. B. J. Am. Chem. Soc. 2002, 124, 1889
28. Gelardi, G.; Barker, G.; OBrien, P.; Blakemore, D. C. Org. Lett. 2013, 15, 5424
29. Dieter, R. K.; Topping, C. M.; Chandupatla, K. R.; Lu, K. J. Am. Chem. Soc. 2001, 123, 5132
30. Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-y. J. Am. Chem. Soc. 2006, 128, 3538
31. Klapars, A.; Campos, K. R.; Waldman, J. H.; Zewge, D.; Dormer, P. G.; Chen, C.-y J. Org. Chem. 2008, 73, 4986
32. Coldham, I.; Leonori, D. Org. Lett. 2008, 10, 3923
33. Millet, A.; Larini, P.; Clot, E.; Baudoin, O. Chem. Sci. 2013, 4, 2241
34. Seel, S.; Thaler, T.; Takatsu, K.; Zhang, C.; Zipse, H.; Straub, B. F.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2011, 133, 4774
35. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154
36. Godula, K.; Sames, D. Science 2006, 312, 67
37. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
38. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
39. Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362
40. Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935
41. Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220
42. Prokopcová, H.; Bergman, S. D.; Aelvoet, K.; Smout, V.; Herrebout, W.; Van der Veken, B.; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2010, 16, 13063
43. Peschiulli, A.; Smout, V.; Storr, T. E.; Mitchell, E. A.; Eliás, Z.; Herrebout, W.; Berthelot, D.; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2013, 19, 10378
44. Smout, V.; Peschiulli, A.; Verbeeck, S.; Mitchell, E. A.; Herrebout, W.; Bultinck, P.; Vande Velde, C. M. L.; Berthelot, D.; Meerpoel, L.; Maes, B. U. W. J. Org. Chem. 2013, 78, 9803
45. Payne, P. R.; Garcia, P.; Eisenberger, P.; Yim, J. C. H.; Schafer, L. L. Org. Lett. 2013, 15, 2182
46. Snieckus, V.; Cuevas, J. C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896
47. Yoshikai, N.; Mieczkowski, A.; Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 5568
48. Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Am. Chem. Soc. 2005, 127, 11610
49. Kamon, T.; Irifune, Y.; Tanaka, T.; Yoshimitsu, T. Org. Lett. 2011, 13, 2674
50. Bertrand, S.; Hoffmann, N.; Pete, J.-P. Eur. J. Org. Chem. 2000, 2227
51. Marinkovic, S.; Hoffmann, N. Chem. Commun. 2001, 1576
52. McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114
53. Jurberg, I. D.; Peng, B.; Wöstefeld, E.; Wasserloos, M.; Maulide, N. Angew. Chem., Int. Ed. 2012, 51, 1950
54. Deb, I.; Das, D.; Seidel, D. Org. Lett. 2011, 13, 812
55. Zhang, C.; Das, D.; Seidel, D. Chem. Sci. 2011, 2, 233
56. Ma, L.; Chen, W.; Seidel, D. J. Am. Chem. Soc. 2012, 134, 15305
57. Das, D.; Sun, A. X.; Seidel, D. Angew. Chem., Int. Ed. 2013, 52, 3765
58. Das, D.; Seidel, D. Org. Lett. 2013, 15, 4358
59. Chen, W.; Wilde, R. G.; Seidel, D. Org. Lett. 2013, 16, 730
60. Hannedouche, J.; Schulz, E. Chem.-Eur. J. 2013, 19, 4972
61. Schultz, D. M.; Wolfe, J. P. Synthesis 2012, 44, 351l
62. Wolfe, J. P.; Neukom, J. D.; Mai, D. H. In Catalyzed Carbon-Heteroatom Bond Formation; Wiley-VCH Verlag: Weinheim, 2010; p 1.
63. Zhai, H.; Borzenko, A.; Lau, Y. Y.; Ahn, S. H.; Schafer, L. L. Angew. Chem., Int. Ed. 2012, 51, 12219
64. Hennessy, E. T.; Betley, T. A. Science 2013, 340, 591
65. Ortiz de Montellano, P. R., Ed. Cytochrome P450: Structure, Mechanism, and Biochemistry, 4th ed.; Kluwer Academic/Plenum: New York, 2005.
66. Groves, J. T.; McClusky, G. A.; White, R. E.; Coon, M. J. Biochem. Biophys. Res. Commun. 1978, 81, 154
67. Wijtmans, R.; Vink, M. K. S.; Schoemaker, H. E.; van Delft, F. L.; Blaauw, R. H.; Rutjes, F. P. J. T. Synthesis 2004, 641
68. Crestey, F. o.; Witt, M.; Jaroszewski, J. W.; Franzyk, H. J. Org. Chem. 2009, 74, 5652
69. Ghorai, M. K.; Shukla, D.; Das, K. J. Org. Chem. 2009, 74, 7013
70. Kashima, C.; Harada, K. J. Chem. Soc., Perkin Trans. 1 1988, 1521
71. Sawant, R. T.; Stevenson, J.; Odell, L. R.; Arvidsson, P. I. Tetrahedron: Asymmetry 2013, 24, 134
72. Lai, J. T. Synthesis 1984, 122
73. Nozulak, J.; Vigouret, J. M.; Jaton, A. L.; Hofmann, A.; Dravid, A. R.; Weber, H. P.; Kalkman, H. O.; Walkinshaw, M. D. J. Med. Chem. 1992, 35, 480
74. Bouron, E.; Goussard, G. r.; Marchand, C.; Bonin, M.; Panneconcke, X.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1999, 40, 7227
75. Sakai, K.; Yoneda, N. Chem. Pharm. Bull. 1981, 29, 1554
76. Hoyt, S. B.; London, C.; Gorin, D.; Wyvratt, M. J.; Fisher, M. H.; Abbadie, C.; Felix, J. P.; Garcia, M. L.; Li, X.; Lyons, K. A.; McGowan, E.; MacIntyre, D. E.; Martin, W. J.; Priest, B. T.; Ritter, A.; Smith, M. M.; Warren, V. A.; Williams, B. S.; Kaczorowski, G. J.; Parsons, W. H. Bioorg. Med. Chem. Lett. 2007, 17, 4630
77. OReilly, M. C.; Lindsley, C. W. Tetrahedron Lett. 2012, 53, 1539
78. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199
79. Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2008, 47, 3784
80. Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Org. Lett. 2008, 11, 257
81. Bagnoli, L.; Scarponi, C.; Rossi, M. G.; Testaferri, L.; Tiecco, M. Chem.-Eur. J. 2011, 17, 993
82. Ruider, S. A.; Müller, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2013, 52, 11908
83. Vo, C.-V. T.; Mikutis, G.; Bode, J. W. Angew. Chem., Int. Ed. 2013, 52, 1705
84. Vo, C.-V. T.; Luescher, M. U.; Bode, J. W. Nat. Chem. 2014, 10.1038/nchem.1878
85. Luescher, M. U.; Vo, C.-V. T.; Bode, J. W. Org. Lett. 2014, 16, 1236-1239