Transition-metal-free synthesis of substituted pyridines via ring expansion of 2-allyl-2H-azirines

Organic Letters

Volumn 16, Issue 13, 2014, Pages 3432-3435

  Jiang, Yaojia ^a   Park, Cheol Min ^c   Loh, Teck Peng ^a,b  

^a Nanyang Technological University   (Singapore)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^c Ulsan National Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AZIRINES; CATALYSIS; MOLECULAR STRUCTURE; PYRIDINES;

EID: 84903689092     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501010k     Document Type: Article

References (71)

1. Michael, J. P. Nat. Prod. Rep. 2005, 22, 627-646
2. Olbe, L.; Carlsson, E.; Lindberg, P. Nature 2003, 2, 132-139
3. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4 th ed.; Blackwell Science: Cambridge, 2000; pp 63-120.
4. Roth, H. J.; Kleemann, A. Drug Synthesis, in Pharmaceutical Chemistry; John Wiley and Sons: New York, 1988; Vol. 1.
5. Kral, K.; Hapke, M. Angew. Chem., Int. Ed. 2011, 50, 2434-2435
6. Hill, M. D. Chem.-Eur. J. 2010, 16, 12052-12062
7. Groenendaal, B.; Ruijter, E.; Orru, R. V. A. Chem. Commun. 2008, 5474-5489
8. Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085-1092
9. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4648
10. Spitzner, D. In Science of Synthesis; Black, D.; Georg, StC., Eds.; Thieme Verlag, Stuttgart, 2005; pp 11-284.
11. Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787-3802
12. Henry, G. D. Tetrahedron 2004, 60, 6043-6061
13. Frederic, L. M.; Allais, C.; Constantieux, T.; Rodriguez, J. Chem. Commun. 2008, 4207-4209
14. Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957-4980
15. Sausins, A.; Duburs, G. Heterocycles 1988, 27, 269-289
16. Wei, Y.; Yoshikai, N. J. Am. Chem. Soc. 2013, 135, 3756-3759
17. Loy, N. S. Y.; Singh, A.; Xu, X.; Park, C.-M. Angew. Chem., Int. Ed. 2013, 52, 2212-2216
18. Yamamoto, S.; Okamoto, K.; Murakoso, M.; Kuninobu, Y.; Takai, K. Org. Lett. 2012, 14, 3182-3185
19. Gati, W.; Rammah, M. M.; Rammah, M. B.; Couty, F.; Evano, G. J. Am. Chem. Soc. 2012, 134, 9078-9081
20. Kim, D. S.; Park, J. W.; Jun, C. H. Chem. Commun. 2012, 48, 11334-11336
21. Ohashi, M.; Takeda, I.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 18018-18021
22. Wang, C.; Li, X.; Wu, F.; Wan, B. Angew. Chem., Int. Ed. 2011, 50, 7162-7166
23. Nakamura, I.; Zhang, D.; Terada, M. J. Am. Chem. Soc. 2010, 132, 7884-7886
24. Sakai, T.; Danheiser, R. L. J. Am. Chem. Soc. 2010, 132, 13203-13205
25. Sha, F.; Huang, X. Angew. Chem., Int. Ed. 2009, 48, 3458-3461
26. Wang, Y.-F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570-12572
27. Chiba, S.; Xu, Y.-J.; Wang, Y.-F. J. Am. Chem. Soc. 2009, 131, 12886-12887
28. Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918-6919
29. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645-3651
30. Barluenga, J.; Fernández-Rodríguez, M. á.; García-García, P.; Aguilar, E. J. Am. Chem. Soc. 2008, 130, 2764-2675
31. Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc. 2008, 130, 8602-8603
32. Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918-6919
33. Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc. 2007, 129, 10096-10097
34. Trost, B. M.; Gutierrez, A. C. Org. Lett. 2007, 9, 1473-1476
35. Chang, H.-T.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2007, 9, 505-508
36. Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 4592-4593
37. McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2005, 127, 5030-5031
38. Yamamoto, Y.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6189-6190
39. Khlebnikov, A. F.; Novikov, M. S. Tetrahedron 2013, 69, 3363-3401
40. Padwa, A. Comprehensive Heterocyclic Chemistry III; Elsevier, Ltd.: Amsterdam, 2008; pp 1-104.
41. Skepper, C. K.; Molinski, T. F. J. Org. Chem. 2008, 73, 2592-2597
42. Melo, T. M. V. D. P. E.; Gonsalves, A. M. R. Curr. Org. Synth. 2004, 1, 275-292
43. Palacios, F.; Retana, A. M. O.; Marigorta, E. M.; Santos, J. M. Org. Prep. Proced. Int. 2002, 34, 219-269
44. Gilchrist, T. L. Aldrichimica Acta 2001, 51-55
45. Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford; 1984; Vol. 7, pp 47-93.
46. Padwa, A. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL, 2010; Vol. 99, pp 1-31.
47. Gilchrist, T. L.; Alves, M. J. In Organic Azides; John Wiley & Sons Ltd.: Chichester, U.K., 2010; pp 167-187.
48. Singh, J. G. S.; D'hooghe, M.; Kimpe, N. D. Chem. Rev. 2007, 107, 2080-2135
49. Palacios, F.; Retana, A. M. O.; Marigorta, E. M.; Santos, J. M. Eur. J. Org. Chem. 2001, 2401-2414
50. Anderson, D. J.; Hassner, A. Synthesis 1975, 483-495
51. Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 3312-3315
52. Brahma, S.; Ray, J. K. J. Heterocycl. Chem. 2008, 45, 311-317
53. Stevens, K. L.; Jung, D. K.; Alberti, M. J.; Badiang, J. G.; Peckham, G. E.; Veal, J. M.; Cheung, M.; Harris, P. A.; Chamberlain, S. D.; Peel, M. R. Org. Lett. 2005, 7, 4753-4756
54. Padwa, A.; Stengel, T. Tetrahedron Lett. 2004, 45, 5991-5993
55. Jiang, Y.; Park, C.-M. Chem. Sci. 2014, 5, 2347-2351
56. Jiang, Y.; Chan, W. C.; Park, C.-M. J. Am. Chem. Soc. 2012, 134, 4104-4107
57. Jana, S.; Clements, M. D.; Sharp, B. K.; Zheng, N. Org. Lett. 2010, 12, 3736-3739
58. Chiba, S.; Hattoti, G.; Narasaka, K. Chem. Lett. 2007, 36, 52-53
59. Taber, D. F.; Tian, W. J. Am. Chem. Soc. 2006, 128, 1058-1059
60. Padwa, A.; Smolanoff, J.; Tremper, A. J. Am. Chem. Soc. 1975, 97, 4682-4691
61. Padwa, A.; Carlsen, P. H. J. Tetrahedron Lett. 1978, 19, 433-436
62. Okamoto, K.; Oda, T.; Kohigashi, S.; Ohe, K. Angew. Chem., Int. Ed. 2011, 50, 11470-11473
63. Prechter, A.; Henrion, G.; Bel, P. F.; Gagosz, F. Angew. Chem., Int. Ed. 2014, 53, 4959-4963
64. Shi, Z.-G.; Loh, T.-P. Angew. Chem., Int. Ed. 2013, 52, 8584-8587
65. Winter, A.; Risch, N. Synlett 2003, 1959-1964
66. Neber, P. W.; Huh, G. Justus Liebigs Ann. Chem. 1935, 515, 283-296
67. Neber, P. W.; Burgard, A. Justus Liebigs Ann. Chem. 1932, 493, 281-294
68. Nguyen, Q.; Nguyen, T.; Driver, T. G. J. Am. Chem. Soc. 2013, 135, 620-623
69. Hennessy, E. T.; Betley, T. A. Science 2013, 340, 591-595
70. Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036-2039
71. Sun, K.; Liu, S.; Bec, P. M.; Driver, T. G. Angew. Chem., Int. Ed. 2011, 50, 1702-1706