Vilsmeier-type reaction of dimethylaminoalkenoyl cyclopropanes: One-pot access to 2,3-dihydrofuro [3,2- c ]pyridin-4(5 H)-ones

Organic Letters

Volumn 14, Issue 1, 2012, Pages 370-373

  Huang, Peng ^a   Zhang, Ning ^a   Zhang, Rui ^a   Dong, Dewen ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BIOLOGICAL PRODUCT; CYCLOPROPANE DERIVATIVE; PYRIDINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METHYLATION;

ALKENES; AMINATION; BIOLOGICAL AGENTS; CYCLIZATION; CYCLOPROPANES; METHYLATION; MOLECULAR STRUCTURE; PYRIDINES;

EID: 84855504645     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol203124f     Document Type: Article

References (64)

1. Maffrand, J.-P. (Parcor) GB 2023599, 1980.
2. Surman, M. D.; Freeman, E. E.; Grabowski, J. F.; Hadden, M.; Henderson, A. J.; Jiang, G.; Jiang, X.; Luche, M.; Khmelnitsky, Y.; Vickers, S.; Viggers, J.; Cheetham, S.; Guzzo, P. R. Bioorg. Med. Chem. Lett. 2010, 20, 7015-7019
3. Xiao, D.; Zhu, L.; Wang, S.; Liang, Z.; Hu, W. (Chemizon (BeiJing), LTD.) WO 2010/145197 A1, 2010.
4. Naito, T.; Miyata, O.; Kida, N.; Namoto, K.; Ninomiya, I. Chem. Pharm. Bull. 1990, 38, 2419-2423
5. New, J. S.; Christopher, W. L.; Yevich, J. P.; Butler, R.; Schlemmer, R. F., Jr.; VanderMaelen, C. P.; Cipollina, J. A. J. Med. Chem. 1989, 32, 1147-1156
6. Miyazaki, Y.; Nakano, M.; Sato, H.; Truesdale, A. T.; Stuart, J. D.; Nartey, E. N.; Hightower, K. E.; Kane-Carson, L. Bioorg. Med. Chem. Lett. 2007, 17, 250-254
7. Mavoungou-Gomès, L.; Bruneton, J.; Aicart, M. J. Heterocycl. Chem. 1985, 22, 1233-1236
8. Matsuda, T.; Yamagata, K.; Tomioka, Y.; Yamazaki, M. Chem. Pharm. Bull. 1985, 33, 937-943
9. Yamagata, K.; Okabe, F.; Yamazaki, M. J. Prakt. Chem. 1999, 341, 562-567
10. Hagiwara, H.; Sato, K.; Nishino, D.; Hoshi, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2001, 2946-2957
11. Tang, E.; Huang, X.; Xu, W.-M. Tetrahedron 2004, 60, 9963-9969
12. Conreaux, D.; Belot, S.; Desbordes, P.; Monteiro, N.; Balme, G. J. Org. Chem. 2008, 73, 8619-8622
13. Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565-10569
14. Miyagawa, T.; Nagai, K.; Yamada, A.; Sugihara, Y.; Fukuda, T.; Fukuda, T.; Uchida, R.; Tomoda, H.; Omura, S.; Nagamitsu, T. Org. Lett. 2011, 13, 1158-1161
15. Clive, D. L. J.; Huang, X. Tetrahedron 2002, 58, 10243-10250
16. Clive, D. L. J.; Huang, X. J. Org. Chem. 2004, 69, 1872-1879
17. Snider, B. B.; Che, Q. Org. Lett. 2004, 6, 2877-2880
18. Sakemi, S.; Bordner, J.; DeCosta, D. L.; Dekker, K. A.; Hirai, H.; Inagaki, T.; Kim, Y.-J.; Kojima, N.; Sims, J. C.; Sugie, Y.; Sugiura, A.; Sutcliffe, J. A.; Tachikawa, K.; Truesdell, S. J.; Wong, J. W.; Yoshikawa, N.; Kojima, Y. J. Antibiot. 2002, 55, 6-18
19. Sugie, Y.; Truesdell, S. J.; Wong, J. W.; Yoshikawa, N.; Sugiura, A. (Pfizer, US). Furopyridine Antibacterials. EP 0999212, May 10, 2000.
20. Fukuda, T.; Yamaguchi, Y.; Masuma, R.; Tomoda, H.; Omura, S. J. Antibiot. 2005, 58, 309-314
21. Fukuda, T.; Tomoda, H.; Omura, S. J. Antibiot. 2005, 58, 315-321
22. Wei, Y.; Lin, S.; Zhang, J.; Niu, Z.; Fu, Q.; Liang, F. Chem. Commun. 2011, 47, 12394-12396
23. Liang, F.; Lin, S.; Wei, Y. J. Am. Chem. Soc. 2011, 133, 1781-1783
24. Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578-4579
25. Dong, D.; Bi, X.; Liu, Q.; Cong, F. Chem. Commun. 2005, 3580-3582
26. Bi, X.; Dong, D.; Li, Y.; Liu, Q.; Zhang, Q. J. Org. Chem. 2005, 70, 10886-10889
27. Huang, J.; Liang, Y.; Pan., W.; Yang, Y.; Dong, D. Org. Lett. 2007, 9, 5345-5348
28. Wang, K.; Fu, X.; Liu, J.; Liang, Y.; Dong, D. Org. Lett. 2009, 11, 1015-1018
29. Wang, Y.; Xin, X.; Liang, Y.; Lin, Y.; Duan, H.; Dong, D. Adv. Synth. Catal. 2009, 351, 2217-2223
30. Zhang, R.; Liang, Y.; Zhou, G.; Wang, K.; Dong, D. J. Org. Chem. 2008, 73, 8089-8092
31. Zhang, R.; Zhou, Y.; Liang, Y.; Jiang, Z.; Dong, D. Synthesis 2009, 2497-2500
32. Jones, G.; Stanforth, S. P. The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles. In Organic Reactions; Paquette, L. A., Ed.; John Wiley: New York, 1997; Vol. 49, pp 1-330.
33. Marson, C. M.; Giles, P. R. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, FL, 1994; pp 1-247.
34. Marson, C. M. Tetrahedron 1992, 48, 3659-3726
35. Sayah, B.; Pelloux-Léon, N.; Milet, A.; Pardillos-Guindet, J.; Vallée, Y. J. Org. Chem. 2001, 66, 2522-2525
36. Liu, Y.; Dong, D.; Liu, Q.; Qi, Y.; Wang, Z. Org. Biomol. Chem. 2004, 2, 28-30
37. Sun, S.; Liu, Y.; Liu, Q.; Zhao, Y.; Dong, D. Synlett 2004, 1731-1734
38. Ptaszek, M.; McDowell, B. E.; Lindsey, J. S. J. Org. Chem. 2006, 71, 4328-4331
39. Pinkerton, D. M.; Banwell, M. G.; Willis, A. C. Org. Lett. 2007, 9, 5127-5130
40. Pan, W.; Dong, D.; Wang, K.; Zhang, J.; Wu, R.; Xiang, D.; Liu, Q. Org. Lett. 2007, 9, 2421-2423
41. Xiang, D.; Wang, K.; Liang, Y.; Zhou, G.; Dong, D. Org. Lett. 2008, 10, 345-348
42. Wang, K.; Xiang, D.; Liu, J.; Pan, W.; Dong, D. Org. Lett. 2008, 10, 1691-1694
43. Zhang, R.; Zhang, D.; Guo, Y.; Zhou, G.; Jiang, Z.; Dong, D. J. Org. Chem. 2008, 73, 9504-9507
44. Wang, Y.; Xin, X.; Liang, Y.; Lin, Y.; Zhang, R.; Dong, D. Eur. J. Org. Chem. 2009, 4165-4169
45. Zhang, R.; Zhang, D.; Liang, Y.; Zhou, G.; Dong, D. J. Org. Chem. 2011, 76, 2880-2883
46. Martinez, A. G.; Alvarez, R. M.; Barcina, J. O.; Cerero, S. M.; Vilar, E. T.; Fraile, A. G.; Hanack, M.; Subramanian, L. R. J. Chem. Soc., Chem. Commun. 1990, 1571-1572
47. Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S. Tetrahedron Lett. 1996, 37, 4199-4202
48. Kobayashi, Y.; Nakatani, T.; Tanaka, R.; Okada, M.; Torii, E.; Harayama, T.; Kimachi, T. Tetrahedron 2011, 67, 3457-3463
49. Falmagne, J. B.; Escudero, J.; Taleb-Saharaoui, S.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1981, 20, 879-880
50. Barbaro, G.; Battaglia, A.; Bruno, C.; Giorgianni, P.; Guerrini, A. J. Org. Chem. 1996, 61, 8480-8488
51. For review on iminium triflate, see: Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077-3119
52. DeRoy, P. L.; Charette, A. B. Org. Lett. 2003, 5, 4163-4165
53. Zheng, X.; Kerr, M. A. Org. Lett. 2006, 8, 3777-3779
54. Barbe, G.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 18-19
55. Cui, S.; Wang, J.; Wang, Y. J. Am. Chem. Soc. 2008, 130, 13526-13527
56. Kobayashi, Y.; Harayama, T. Tetrahedron Lett. 2009, 50, 6665-6667
57. Pelletier, G.; Bechara, W. S.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 12817-12819
58. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174-1187
59. Wong, H. N. C.; Hon, M. Y.; Tse, C. W.; Yip, Y. C. Chem. Rev. 1989, 89, 165-198
60. Yadav, V. K.; Balamurugan, R. Org. Lett. 2001, 3, 2717-2719
61. Sydnes, L. K. Chem. Rev. 2003, 103, 1133-1150
62. Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565-4568
63. Bowman, R. K.; Johnson, J. S. Org. Lett. 2006, 8, 573-576
64. Zhang, Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew. Chem., Int. Ed. 2007, 46, 1726-1729