A divergent synthesis of γ-iminolactones, dihydroquinolin-2-ones, and γ-lactames from β-hydroxymethylcyclopropanylamides

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 8005-8009

  Xiong, Tao ^a   Zhang, Qian ^a   Zhang, Zhiguo ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; SYNTHESIS (CHEMICAL); TIN COMPOUNDS; TITANIUM COMPOUNDS;

DIHYDROQUINOLIN; DIVERGENT SYNTHESIS; HYDROXYMETHYLCYCLOPROPANYLAMIDES; IMINOLACTONES;

KETONES;

AMIDE; CYCLOPROPANE DERIVATIVE; GAMMA LACTAM DERIVATIVE; IMINE; LACTONE DERIVATIVE; QUINOLINE DERIVATIVE; SODIUM IODIDE; TIN CHLORIDE;

ARTICLE; BIOTRANSFORMATION; CYCLIZATION; FRIEDEL CRAFTS REACTION; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; SYNTHESIS; X RAY DIFFRACTION;

EID: 35348900083     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701495s     Document Type: Article

References (80)

1. For reviews, see: (a) Sydnes, L. K. Chem. Rev. 2003, 103, 1133-1150.
2. (b) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603-1624.
3. (c) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196.
4. (d) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
5. (e) Reichelt, A.; Martin, S. F. Acc. Chem. Res. 2006, 39, 433-442.
6. (f) Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321-347.
7. (g) Wong, H. N. C.; Hon, M. Y.; Tse, C. W.; Yip, Y. C. Chem. Rev. 1989, 89, 165-198.
8. For some recent results, see: (a) Ogoshi, S.; Nagata, M.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 5350-5351.
9. (b) Liu, L.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 5348-5349.
10. (c) Ma, S.; Zhang, J. Angew. Chem., Int. Ed. 2003, 42, 183-187.
11. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174-1187.
12. (a) Alonso, M. E.; Morales, A. J. Org. Chem. 1980, 45, 4530-4532.
13. (b) Yadav, V. K.; Balamurugan, R. Org. Lett. 2001, 3, 2717-2719.
14. (c) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565-4568.
15. (d) Pittman, C. U.; McManus, S. P. J. Am. Chem. Soc. 1969, 91, 5915-5918.
16. (e) Honda, M.; Naitou, T.; Hoshino, H.; Takagi, S.; Segi, M.; Nakajima, T. Tetrahedron Lett. 2005, 46, 7345-7348.
17. (f) Bowman, R. K.; Johnson, J. S. Org. Lett. 2006, 8, 573-576.
18. (g) Yadav, A. K.; Peruncheralathan, S.; Ha, H.; Junjappa, H. J. Org. Chem. 2007, 72, 1388-1394.
19. (h) Liu, L.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 5348-5349.
20. (i) Ogoshi, S.; Nagata, M.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 5350-5351.
21. j) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2006, 45, 6788-6790.
22. (k) Zhang, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2006, 45, 6704-6707.
23. (a) Yang, Y.-H.; Shi, M. J. Org. Chem. 2005, 70, 8645-8648.
24. (b) Kirkland, T. A.; Colucci, J.; Geraci, L. S.; Marx, M. A.; Schneider, M.; Kaelin, D. E., Jr.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 12432-12433.
25. (c) Zheng, X.; Kerr, M. A. Org. Lett. 2006, 8, 3777-3779.
26. (d) Zhang, M.-X.; Eaton, P. E. Angew. Chem., Int. Ed. 2002, 41, 2169-2171.
27. (e) Concellon, J. M.; Rodriguez-Solla, H.; Llavona, R. J. Org. Chem. 2003, 68, 1132-1133.
28. (a) Zhang, Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew. Chem., Int. Ed 2007, 46, 1726-1729.
29. (b) Pan, W.; Dong, D.; Wang, K.; Zhang, J.; Wu, R.; Xiang, D.; Liu, Q. Org. Lett. 2007, 9, 2421-2423.
30. (a) Kanemoto, S.; Shimizu, M.; Yoshioka, H. Tetrahedron Lett. 1987, 28, 6313-6316.
31. (b) Hardouin, C.; Taran, F.; Doris, E. J. Org. Chem. 2001, 66, 4450-4452.
32. (c) Bernard, A. M.; Frongia, A.; Secci, F.; Piras, P. P. Chem. Commun. 2005, 3853-3855.
33. (a) Sarel, S.; Yovell, J.; Sarel-Imber, M. Angew. Chem., Int. Ed. Engl. 1968, 7, 577-588.
34. (b) Wong, H. N. C.; Hon, M. Y.; Tse, C. W.; Yip, Y. C.; Tanko, J.; Huldicky, T. Chem. Rev. 1989, 89, 165-198.
35. Yadav, V. K.; Kumar, N. V. J. Am. Chem. Soc. 2004, 126, 8652-8653.
36. (a) Buchmann, W.; Desmazieres, B.; Morizur, J.-P.; Nguyen, H. A.; Cheradame, H. Macromolecules 2001, 34, 2783-2791.
37. (b) Angle, S. R.; Frutos, R. P. J. Chem. Soc., Chem. Commun. 1993, 171-172.
38. (c) Keller, A. J. Mol. Catal. 1991, 64, 171-178.
39. (a) Chang, J.-W.; Jang, D.-P.; Uang, B.-J.; Liao, F.-L.; Wang, S.-L. Org. Lett. 1999, 1, 2061-2063.
40. (b) Du, Y.; Kong, F. J. Carbohydr. Chem. 1995, 14, 341-352.
41. (c) Thompson, J. E. J. Org. Chem. 1967, 32, 3947-3950.
42. (a) Uto, K.; Sakamoto, T.; Matsumoto, K.; Kikugawa, Y. Heterocycles 1996, 43, 633-640.
43. (b) Tashiro, M. Synthesis 1979, 921-936.
44. (c) Park, B.-D.; Lee, H.-I.; Ryoo, S.-J.; Lee, Y.-S. Tetrahedron Lett. 1997, 38, 591-594.
45. (a) Mukaiyama, T.; Narasaka, K. Org. Synth. 1987, 65, 6-10.
46. (b) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747-5750.
47. (c) Uno, H.; Baldwin, J. E.; Churcher, I.; Russell, A. T. Synlett 1997, 390-393.
48. (d) Maeda, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 6429-6431.
49. (e) Paterson, I. Tetrahedron 1988, 44, 4207-4219.
50. (a) Haynes, R. K.; King, G. R.; Vonwiller, S. C. J. Org. Chem. 1994, 59, 4743-4748.
51. (b) Mandal, A. B.; Gomez, A.; Trujillo, G.; Mendez, F.; Jimenez, H. A.; de Rosales, M.; Martinez, R.; Delgado, F.; Tamariz, J. J. Org. Chem. 1997, 62, 4105-4115.
52. (c) Liu, H. J.; Han, Y. Tetrahedron Lett. 1993, 34, 423-426.
53. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-3706.
54. (e) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126.
55. (f) Conde, S.; Corral, C.; Madronero, R. Synthesis 1974, 28-29.
56. (a) Li, W.-D. Z.; Yang, J.-H. Org. Lett. 2004, 6, 1849-1852.
57. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C. Chem. Rev. 1989, 89, 165-198.
58. (c) Li, W.-D. Z.; Peng, Y. Org. Lett. 2005, 7, 3069-3072.
59. (d) Ranu, B. C.; Banerjee, S. Eur. J. Org. Chem. 2006, 3012-3015.
60. For details for the preparation of 1-(1-hydroxyethyl)-N-(2- methoxyphenyl)cyclopropanecarboxamide (5) and β- hydroxymethylcyclopropanylamides 1, please see the Supporting Information and also see: (a) Liu, J.; Liang, F.; Liu, Q.; Li, B. Synlett 2007, 156-160.
61. (b) Liu, J.; Wang, M.; Li, B.; Liu, Q.; Zhao, Y. J. Org. Chem. 2007, 72, 4401-4405.
62. For the preparation of condensation adducts of 1-acetyl-N-arylcyclopropanecarboxamides with aromatic aldehydes, please see: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578-4579.
63. (b) Bi, X.; Liu, Q.; Sun, S.; Liu, J.; Pan, W.; Zhao, L.; Dong, D. Synlett 2005, 49-54.
64. For selected examples for the synthesis of γ-iminolactones, see: (a) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899-907.
65. (b) Ma, S.; Gu, Z.; Yu, Z. J. Org. Chem. 2005, 70, 6291-6294.
66. (c) Tang, Y.; Li, C.-Z. Tetrahedron Lett. 2006, 47, 3823-3825.
67. (d) Ma, S.; Xie, H. J. Org. Chem. 2002, 67, 6575-6578.
68. (a) Bartoli, G.; Bellucci, M. C.; Petrini, M.; Marcantoni, E.; Sambri, L.; Torregiani, E. Org. Lett. 2000, 2, 1791-1793.
69. (b) Kamal, A.; Prasad, B. R.; Ramana, A. V.; Babu, A. H.; Reddy, K. S. Tetrahedron Lett. 2004, 45, 3507-3509.
70. (c) Node, M.; Kajimoto, T.; Nishide, K.; Fujita, E.; Fuji, K. Tetrahedron Lett. 1984, 25, 219-222.
71. Selected examples: (a) Barluenga, J.; Alonso, J.; Fañanás, F. J. J. Am. Chem. Soc. 2003, 125, 2610-2616.
72. (b) Doyle, M. P.; Yan, M.; Hu, W.; Gronenberg, L. S. J. Am. Chem. Soc. 2003, 125, 4692-4693.
73. (c) Denmark, S. E.; Pan, W. Org. Lett. 2003, 5, 1119-1122.
74. (d) Zhang, Y.; Raines, A. J.; Flowers, II, R. A. Org. Lett. 2003, 5, 2363-2365.
75. (e) Ma, S.; Wang, G. Angew. Chem., Int. Ed. 2003, 42, 4215-4217.
76. (f) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22-23.
77. (g) Sun, X. W.; Xu, M. H.; Lin, G. Q. Org. Lett. 2006, 8, 4979-4982.
78. (h) Cuny, G.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2004, 126, 14475-14484.
79. (a) Marti, C.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 11505-11515.
80. (b) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186-3189.