Conjugate addition reactions of N -carbamoyl-4-pyridones and 2,3-dihydropyridones with grignard reagents in the absence of Cu(I) Salts

Journal of Organic Chemistry

Volumn 78, Issue 17, 2013, Pages 8451-8464

  Guo, Fenghai ^a,b   Dhakal, Ramesh C ^a   Dieter, R Karl ^a  

^a CLEMSON UNIVERSITY   (United States)

^b WINSTON SALEM STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,4-ADDITION REACTIONS; CHLOROTRIMETHYLSILANES; CONJUGATE ADDITION; CONJUGATE ADDITION REACTIONS; COPPER CATALYSIS; DIASTEREOMERS; GRIGNARD REAGENT; PIPERIDINONES;

REACTION INTERMEDIATES;

ADDITION REACTIONS;

CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CHLOROTRIMETHYLSILANE; COPPER DERIVATIVE; GRIGNARD REAGENT; PIPERIDONE DERIVATIVE; PYRIDINIUM DERIVATIVE; PYRIDONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CIS TRANS ISOMERISM; CONJUGATION; DIASTEREOISOMER; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PIPERIDINES; PYRIDONES;

EID: 84883756417     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400936z     Document Type: Article

References (93)

1. Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645-1680
2. Watson, P. S.; Jiang, B.; Scott, B. Org. Lett. 2000, 2, 3679-3681
3. Stinson, S. C. C&EN 2001, 79 (20) 45-57
4. Thayer, A. M. C&EN 2007, 85 (32) 11-19
5. Cossy J. Chem. Rec. 2005, 5, 70-80 and references cited therein
6. Pearson, M. S. M.; Mathé-Allainmat, M.; Fargeas, V.; Lebreton, J. Eur. J. Org. Chem 2005, 2159-2191
7. Buffat, M. G. P. Tetrahedron 2004, 60, 1701-1729
8. Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003-8030
9. Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953-2989
10. Laschat, S.; Dickner, T. Synthesis 2000, 1781-1813
11. Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc. Chem. Commun. 1998, 633-640
12. Sebesta, R.; Pizzuti, M.; Boersma, A. J.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2005, 1711-1713
13. Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2005, 7, 2433-2435
14. Alexakis, A.; Backvall, J. E.; Krause, N.; Pamies, O.; Dieguez, M. Chem. Rev. 2008, 108, 2796-2823 and references cited therein
15. Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; John Wiley & Sons: New York, 2002; Chapter 7, pp 224-258.
16. Krause, N.; Hoffmann-Roder, A. Synthesis 2001, 171-196
17. Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061
18. Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824-2852 and references cited therein
19. Lopez, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2007, 40, 179-188
20. Duncan, A. P.; Leighton, J. L. Org. Lett. 2004, 6, 4117-4119 and references cited therein
21. Lopez, F.; Harutyunyan, S. R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2005, 44, 2752-2756
22. Brown, M. K.; Degrado, S. J.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2005, 44, 5306-5310
23. Brown, M. K.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 12904-12906
24. Alexakis, A.; Albrow, V.; Biswas, K.; d'Augustin, M.; Prieto, O.; Woodward, S. J. Chem. Soc., Chem. Comm 2005, 2843-2845
25. Joseph, S.; Comins, D. L. Curr. Opin. Drug Discovery Dev. 2002, 5, 870-880
26. Comins, D. L. J. Heterocycl. Chem. 1999, 36, 1491-1500
27. Comins, D. L.; Joseph, S. P. Adv. Nitrogen Heterocycl. 1996, 2, 251-294
28. Donohoe, T. J.; Connolly, M. J.; Walton, L. Org. Lett. 2009, 11, 5562-5565
29. Beifuss, U.; Ledderhose, S. Synlett 1997, 313-315
30. Klegraf, E.; Follmann, M.; Schollmeyer, D.; Kunz, H. Eur. J. Org. Chem. 2004, 3346-3360
31. Focken, T.; Charette, A. B. Org. Lett. 2006, 8, 2985-2988
32. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719-4728
33. Dieter, R. K.; Guo, F. J. Org. Chem. 2009, 74, 3843-3848
34. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6019-6022
35. Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032
36. Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Tetrahedron 1989, 45, 349-362
37. House, H. O.; Wilkins, J. M. J. Org. Chem. 1978, 43, 2443-2454
38. Alvarez, M.; Ajana, W.; Lopez-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917-919
39. Lim, S. H.; Curtis, M. D.; Beak, P. Org. Lett. 2001, 3, 711-714
40. Barbier, P. C. R. Hebd. Seances Acad. Sci 1899, 128, 110
41. Grignard, V. C. R. Hebd. Seances Acad. Sci. 1900, 130, 1322
42. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320
43. Parfenova, L. V.; Pechatkina, S. V.; Khalilov, L. M.; Dzhemilev, U. M. Russ. Chem. Bull., Int. Ed. 2005, 54, 316-327
44. Collins, S. W.; Alger, T. D.; Grant, D. M.; Kuhlmann, K. F.; Smith, J. C. J. Phys. Chem. 1975, 79, 2031-2037
45. Mallwitz, F.; Grasmuller, M.; Ismeier, J. R.; Eckelt, R.; Nuyken, O.; Goedel, W. A. Macromol. Chem. Phys. 1999, 200, 1014-1022
46. van Niel, M. B.; Collins, I.; Beer, M. S.; Broughton, H. B.; Cheng, S. K. F.; Goodacre, S. C.; Heald, A.; Locker, K. L.; MacLeod, A. M.; Morrison, D.; Moyes, C. R.; O'Connor, D.; Pike, A.; Rowley, M.; Russell, M. G. N.; Sohal, B.; Stanton, J. A.; Thomas, S.; Verrier, H.; Watt, A. P.; Castro, J. L. J. Med. Chem. 1999, 42, 2087-2104
47. Comins, D. L.; Fulp, A. B. Org. Lett. 1999, 1, 1941-1943
48. Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240-6241
49. Ma, D.; Zhu, W. Tetrahedron Lett. 2003, 44, 8609-8612
50. Sebesta, R.; Pizzuti, M.; Boersma, A. J.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2005, 1711-1713
51. Kranke, B.; Hebrault, D.; Schultz-Kukula, M.; Kunz, H. Synlett 2004, 671-674
52. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H.; Minnaard, A. J. Org. Lett. 2005, 7, 2433-2435
53. Goualt, N.; Le Roch, M.; Cheignon, A.; Uriac, P.; David, M. Org. Lett. 2011, 13, 4371-4373
54. McCall, W. S.; Grillo, T. A.; Comins, D. L. Org. Lett. 2008, 10, 3255-3257
55. Hamblett, C. L.; Sloman, D. L.; Kliman, L. T.; Adams, B.; Ball, R. G.; Stanton, M. G. Tetrahedron Lett. 2007, 48, 2079-2082
56. Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445-7447 and references cited therein
57. Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867-8878
58. Ayerbe, M.; Morao, I.; Arrieta, A.; Linden, A.; Cossio, P. Tetrahedron Lett. 1996, 37, 3055-3058
59. Pearson, A. J; Protasiewicz, J. D.; Updegraff, J.; Zhang, M. Tetrahedron Lett. 2007, 48, 5569-5572
60. Cao, X.; Liu, F.; Lu, W.; Chen, G.; Yu, G.-A.; Liu, S. H. Tetrahedron 2008, 64, 5629-5636
61. Reid, G. P.; Brear, K. W.; Robins, D. J. Tetrahedron: Asymmetry 2004, 15, 793-801
62. Iqbal, M.; Duffy, P.; Evans, P.; Cloughley, G.; Allan, B.; Lledo, A.; Verdaguer, X.; Riera, A. Org. Biomol. Chem. 2008, 6, 4649-4661
63. Kikuchi, M.; Niikura, S.; Chiba, N.; Terauchi, N.; Asaoka, M. Chem. Lett. 2007, 36, 736-737
64. Fleming, F. F.; Gudipati, V.; Steward, O. W. Tetrahedron 2003, 59, 5585-5593
65. Fleming, F. F.; Wang, Q.; Steward, O. W. J. Org. Chem. 2003, 68, 4235-4238
66. Fleming, F. F.; Gudipati, V.; Steward, O. W. Tetrahedron 2003, 59, 5585-5593
67. Morales-Rios, M. J.; Santos-Sanchez, N. F.; Fragoso-Vazquez, M. J.; Alagille, D.; Villagomez-Ibarra, J. R.; Joseph-Nathan, P. Tetrahedron 2003, 59, 2843-2853
68. Sibi, M. P.; Asano, Y. J. Am. Chem. Soc. 2001, 123, 9708-9709
69. Ocejo, M.; Carrillo, L.; Badia, D.; Vicario, J. L.; Fernandez, N.; Reyes, E. J. Org. Chem. 2009, 74, 4404-4407
70. Tomioka, K.; Shioya, Y.; Nagaoka, Y.; Yamada, K.-I. J. Org. Chem. 2001, 66, 7051-7054 and refereces cited therein
71. Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061
72. Csaky, A. G.; de la Herran, G.; Murcia, M. C. Chem. Soc. Rev. 2010, 39, 4080-4102
73. Kaiser, E., Sr.; Picart, F.; Kubiak, T.; Tam, J. P.; Merrifield, R. B. J. Org. Chem. 1993, 58, 5167-5175
74. Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024
75. Eriksson, M.; Johansson, A.; Nilsson, M.; Olsson, T. J. Am. Chem. Soc. 1996, 118, 10904-10905
76. Venkatraj, M.; Ponnuswamy, S.; jeyaraman, R. Indian J. Chem. 2008, 47B, 411-426
77. Ponnuswamy, S.; Venkatraj, M.; Jeyaraman, R. Indian J. Chem. 2002, 41B, 614-627
78. Jeyaraman, R.; Ponnuswamy, S. Indian J. Chem. 1997, 36B, 730-737
79. Belostotskii, A. M. Trends Heterocycl. Chem. 2005, 10, 23-45
80. Delpuech, J.-J. In Cyclic Organonitrogen Stereodynamics; Lambert, J. B.; Takeuchi, Y. Eds.; VCH: New York, 1992; Chapter 7, pp 169-252.
81. Nelson, J. H. Nuclear Magnetic Resonance Spectroscopy; Prentice Hall: Upper Saddle River, NJ, 2003; Chapter 10, pp 240-242.
82. Gartner, T.; Gschwind, R. M. In The Chemistry of Organocopper Compounds; Rappoport, Z.; Marek, I., Eds.; John Wiley & Sons: Chichester, 2009; Chapter 4, pp 163-216.
83. The dihedral angles shown in Table 5 were obtained from "a molecular mechanics minimizer based on the SYBYL force field from Tripos, Inc." Spartan User's Guide, Version 4.1; WAVEFUNCTION, Inc.: Irvine, CA, 1995.
84. Lin, H.; Paquette, L. A. Synth. Commun. 1994, 24 (17) 2503-2506
85. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232
86. Steinmetz, M. G.; Mayes, R. T. J. Am. Chem. Soc. 1985, 107, 2111-2121
87. Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333-4339
88. Arnold, L. A.; Imbos, R.; Mandoli, A.; Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 2865-78
89. Haider, A.; Cornuz, G.; Wyler, H. Helv. Chim. Acta 1975, 58, 1287-1292
90. Matsumae, H.; Mori, Y.; Matsuyama, K.; Moriyama, N. WO2007139211A1, 2007.
91. Alvaro, G.; Arista, L.; Cardullo, F.; D'Adamo, L.; Feriani, A.; Giovannini, R.; Seri, C. WO2004099143A1, 2004.
92. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109-1117
93. Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919-5922